2,3-Dihydro-1-benzofuran-5-carbaldehyde [C9H8O2]

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Citations (27)

References

1

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Rx-ID: 9180608 Find similar reactions

100%

With trichlorophosphate

T=70 - 90°C; 9.5 h; Hide Experimental Procedure

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Takeda Pharmaceutical Company Limited

Patent: EP1792899 A1, 2007 ; Location in patent: Page/Page column 11 ; Title/Abstract

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1:

2,3-Dihydrobenzofuran (100 g, 832 mmol) and N,N-dimethylformamide (134 g, 1830 mmol) were mixed and heated, and phosphorus oxychloride (255 g, 1643 mmol) were added thereto at an inner temperature of 70 to 80°C over 2 hrs.

The reaction mixture was heated at an inner temperature of 80 to 90°C and stirred for 7.5 hrs.

Then, the resulting mixture was added dropwise to water (1000 g) under cooling, and stirred at room temperature for 5 hrs.

The resulting mixture was extracted with toluene, and the extract was washed sequentially with water, saturated sodium bicarbonate aqueous solution and water, and the organic layer was concentrated under vacuum to give a toluene solution of the title compound (amount 340 g, apparent yield 100percent).

98%

Stage #1: With trichlorophosphate

T=30 - 70°C; Stage #2: With water in N,N-dimethylformamide

T=20°C; 1 h;

USV LIMITED; SATHE, Dhananjay, Govind; BHISE, Nandu, Baban; GATNE, Parag, Sukumar; PATNEKAR, Subodh, Shashikant; DEORE, Raviraj, Bhatu; MAHAJAN, Anil, Dinkar

Patent: WO2010/41271 A2, 2010 ; Location in patent: Page/Page column 28 ;

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Title/Abstract

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1:

To a solution of 2,3-dihydrobenzofuran (600.0 g, 4.99 moles) in N,N-dimethylformamide(804 g, 10.98 moles) was added drop-wise phosphorous oxychloride (1530 g, 9.96 moles) over a period of 45 min maintaining the temperature of reaction mixture between 30- 35°C. The mixture was slowly heated to 7O0C and stirred for 8 hr. The mixture was cooled to room temperature and poured into 8 lit of ice-cold water and stirred for 1 hr. The reaction mixture was saturated with sodium chloride and then the product was extracted with ethyl acetate (6L). The extract was washed with saturated aqueous solution of sodium bicarbonate (1.5 L) and concentrated under reduced pressure to obtain (725 g, 98percent) of the title compound.

93%

With trichlorophosphate

T=75°C; Vilsmeier-Haack Formylation; 12 h;

Chen, Wen; Yang, Li-Juan; Li, Yan; Wang, Xue-Quan; Wang, Shao-Jie; Wan, Wei-Chao; Zhang, Hong-Bin; Yang, Xiao-Dong

Letters in Drug Design and Discovery, 2013 , vol. 10, # 7 p. 561 - 571 Title/Abstract

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93%

T=85°C; 12 h; Cooling with ice; Hide Experimental Procedure

Yunnan University; Yang Xiaodong; Zhang Hongbin; Chen Wen; Wang Xuequan; Yang Lijuan; Li Liang

Patent: CN102766135 B, 2017 ; Location in patent: Paragraph 0035-0036 ; Title/Abstract

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1.1:Preparation of 5 - Aldehyde Dihydrobenzofuran

(31.4 ml, 0.333πο1) was slowly added dropwise to N, N-dimethylformamide (28.4 ml, 0.366 mol). After 10 minutes of reaction, the mixture was slowly added dropwise , 3-dihydrobenzofuran (1,20.0g, 0.166πο1), remove the ice bath, heating at 85 ° C stirring reaction for 12 hours, the reaction system into the ice water, add sodium hydroxide solution, adjust the PH value The organic phase was washed with saturated brine, dried over anhydrous Na2S04, filtered and the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (100-200 mesh), petroleum ether-ethyl acetate ( 5: 1) as eluant, to give 5-aldehyde dihydrobenzofuran (2,22.8 g) in a yield of 93percent.

86%

With trichlorophosphate

T=80 - 85°C; 12 h;

Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori

Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4222 - 4239 Title/Abstract

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85%

With trichlorophosphate

T=80 - 85°C; 4 - 5 h; Hide Experimental Procedure

TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.

Patent: WO2008/151170 A2, 2008 ; Location in patent: Page/Page column 45 ; Title/Abstract

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1:

Example 1; Synthesis of 2,3-dihydrobenzofuran-5-carboxaldehdye:Phosphorous oxychloride (255.58 g, 1.666 mol) was slowly added to a solution of DMF (355.0 ml) and 2, 3-dihydrobenzofuran (100 g, 0.833 mol) maintaining the temperature 80-850C. The reaction mixture was stirred for 4-5 hr and the reaction progress monitored by HPLC. The reaction mixture was then poured into ice water and extracted with toluene (2000 ml).

The organic layer was washed with 5percent sodium bicarbonate solution (500 ml) and then 10percent brine solution (500 ml). The organic layer was distilled off under vacuum at 50-600C. A liquid product was isolated.

Yield: 85- 90percent, Purity: 90-92 percent With trichlorophosphate

T=30 - 98°C; 5.16667 h; Hide Experimental Procedure

DR. REDDY'S LABORATORIES LTD.; DR. REDDY'S LABORATORIES, INC.

Patent: WO2008/150953 A1, 2008 ; Location in patent: Page/Page column 29 ; Title/Abstract

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1:

EXAMPLE 1 : Preparation of 2, 3- DIHYDROBENZOFURAN -5- CARBALDEHYDE (FORMULA XII, wherein i1^ represents a single bond); 400 g of 2,3-dihydro benzofuran of Formula XIII (wherein =* represents a single bond) and 566 ml of dimethyl formamide (DMF) were charged into a clean and dry 4 neck round bottom flask followed by stirring for about 5 minutes. 544 ml of phosphorous oxy chloride was slowly added through a dropper for 65 minutes at 3O0C. The reaction solution was heated to 95-98°C followed by stirring for 4 hours for the completion of the reaction. The reaction mass was then cooled to 100C and quenched into ice slowly followed by stirring for 20-30 minutes. 1300 ml of caustic lye was added to the solution at 25 - 350C to adjust the pH of the reaction mass to neutral. The reaction mass was extracted with dichloromethane (3X1000 ml) and separated the organic layer and aqueous layer. The combined organic layer was washed with brine solution (2000 ml). The resultant organic layer was distilled completely below 6O0C to afford 497 g of the title compound.

14.5 g

With phosphorus pentachloride

T=70 - 80°C; 10 h; Hide Experimental Procedure

Hangzhou Duyi Technology Co., Ltd.; Bian Gaofeng; Wang Jian; Zheng Zengying; Li Zhenye

Patent: CN106554345 A, 2017 ; Location in patent: Paragraph 0032-0033 ; Title/Abstract

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4:example 3

Take a 1001 ^ three mouth reaction bottle,2,3-dihydrobenzofuran (128, 0.1111) was dissolved in nitrogen,Nitrogen-dimethylformamide (120 g, 1.64 mil) was placed in a reaction flask,Heated to 70 ° C to 80 ° C in 2 hours with mechanical agitation, In part by adding phosphorus pentachloride / nitrogen,Nitrogen-dimethylformamide mixed formylating reagent (25 g, 0.2 mol).The reaction mixture was incubated for 8 hours.After the reaction,The reaction mixture was added dropwise to ice water (l0 g) and stirred at room temperature for 5 hours.Toluene 50mL extraction,Organic layer followed by water,Saturated aqueous sodium bicarbonate solution and washed with water,Dried over anhydrous sodium sulfate,filter,The organic layer was concentrated to give product 2, 3-dihydrobenzofuran-5-carbaldehyde (14. 5 g, 0.08 mil).This product can be used for the production of lamivudine.

2

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With dipotassium hydrogenphosphate; fac-tris(2phenylpyridinato-N,C2')iridium(III); tris(trimethylsilyl)silane; dimethyl dicarbonate in acetonitrile

T=20°C; 6 h; Schlenk techniqueInert atmosphereSealed tubeIrradiation;

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Rx-ID: 46204100 Find similar reactions

Zhang, Muliang; Li, Nan; Tao, Xingyu; Ruzi, Rehanguli; Yu, Shouyun; Zhu, Chengjian

Chemical Communications, 2017 , vol. 53, # 73 p. 10228 - 10231 Title/Abstract

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3

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With (4,4-dimethyl-2,6-dioxocyclohexyl)-phenyl-iodonium betaine; trimethylsilyl trifluoromethanesulfonate in dichloromethane

T=20°C; Kinetics;

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Rx-ID: 43109628 Find similar reactions

Chelli, Saloua; Troshin, Konstantin; Mayer, Peter; Lakhdar, Sami; Ofial, Armin R.; Mayr, Herbert

Journal of the American Chemical Society, 2016 , vol. 138, # 32 p. 10304 - 10313 Title/Abstract

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A

B

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4

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With tin(IV) chloride in dichloromethane Title compound not separated from

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Tasker, Andrew S.; Sorensen, Bryan K.; Jae, Hwan-Soo; Winn, Martin; Von Geldern, Thomas W.; Dixon, Douglas B.; Chiou, William J.; Dayton, Brian D.; Calzadila, Samuel; Hernandez, Lisa; Marsh, Kennan C.; WuWong, J. Ruth; Opgenorth, Terry J.

Journal of Medicinal Chemistry, 1997 , vol. 40, # 3 p. 322 - 330

byproducts;

Title/Abstract

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Stage #1: 2,3-dihydrobenzo(b)furan With titanium tetrachloride in dichloromethane

T=-5 - 0°C; 0.416667 h; Stage #2: dichloromethoxy methane in dichloromethane

T=0 - 20°C; 2 h; Stage #3: With sodium hydrogencarbonate in dichloromethane; water

VERNALIS RESEARCH LIMITED

Patent: US2005/187282 A1, 2005 ; Location in patent: Page/Page column 8 ; Title/Abstract

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3:

To a stirred solution of 2,3-dihydrobenzo[b]furan (9.4 mL, 83.4 mmol) in dichloromethane (250 mL) under Ar at -5° C. was added dropwise titanium(IV) chloride (18 mL, 167.0 mmol) over 15 min, maintaining the temperature below 0° C. After addition was complete, the red-brown reaction mixture was allowed to stir for a further 10 min before α,α-dichloromethyl methyl ether (8.3 mL, 91.6 mmol) was added dropwise [CAUTIONexotherm] maintaining the temperature below 0° C. Upon complete addition, the vivid crimson reaction mixture was allowed to warm to ambient temperature over 2 h, and was then cautiously poured onto a saturated aqueous solution of sodium bicarbonate (700 mL). The mixture was filtered through a pad of Kieselguhr, which was washed through with dichloromethane. The phases were separated and the aqueous phase was extracted with dichloromethane (2.x.400 mL). The combined organic fractions were washed with brine (300 mL), dried (magnesium sulfate) and concentrated in vacuo to afford a mixture [5-CHO:7-CHO (4:1)] of aldehyde products (11.48 g, 93percent) as a green-black liquid which as used without further purification.

5

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Rx-ID: 9769668 Find similar reactions

98%

With n-butyllithium in tetrahydrofuran; hexane

T=-78 - 20°C;

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Matsunaga, Nobuyuki; Kaku, Tomohiro; Ojida, Akio; Tanaka, Toshimasa; Hara, Takahito; Yamaoka, Masuo; Kusaka, Masami; Tasaka, Akihiro

Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 16 p. 4313 - 4336 Title/Abstract

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6

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With trichlorophosphate in water; N,Ndimethyl-formamide

Takeda Chemical Industries, Ltd.

Patent: EP1334732 A1, 2003 ;

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R.1:Reference Example 1: Reference Example 1: Synthesis of 2,3-dihydrobenzofuran-5-carbaldehyde

Rx-ID: 13289317 Find similar reactions

2,3-Dihydrobenzofuran (100.0 g, 832.3 mmol) and N,N-dimethylformamide (133.8 g, 1830.6 mmol) were mixed and heated, and phosphorus oxychloride (255.2 g, 1643.0 mmol) was added dropwise thereto at an inner temperature of 70 to 80OEC over 2 hours.

The mixture was heated to an inner temperature of 80 to 90OEC, stirred for 7.5 hours, cooled and then added dropwise to 1000 g of water, followed by stirring at room temperature for 5 hours.

After extracting with toluene and washing in turn with water, saturated sodium bicarbonate water and water, the organic layer was concentrated under reduced pressure to obtain a toluene solution of the title compound (yield: 340 g, apparent yield: 100percent) 100%

With trichlorophosphate in water; N,Ndimethyl-formamide

Ishida, Hajime; Fukuta, Makoto

Patent: US2004/18239 A1, 2004 ;

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R.1:Synthesis of 2,3-Dihydrobenzofuran-5-carbaldehyde REFERENCE EXAMPLE 1 Synthesis of 2,3-Dihydrobenzofuran-5-carbaldehyde 2,3-Dihydrobenzofuran (100.0 g, 832.3 mmol) and N,N-dimethylformamide (133.8 g, 1830.6 mmol) were mixed and heated, and phosphorus oxychloride (255.2 g, 1643.0 mmol) was added dropwise thereto at an inner temperature of 70 to 80° C. over 2 hours.

The mixture was heated to an inner temperature of 80 to 90° C., stirred for 7.5 hours, cooled and then added dropwise to 1000 g of water, followed by stirring at room temperature for 5 hours.

After extracting with toluene and washing in turn with water, saturated sodium bicarbonate water and water, the organic layer was concentrated under reduced pressure to obtain a toluene solution of the title compound (yield: 340 g, apparent yield: 100percent) 94%

With sodium hydrogencarbonate; trichlorophosphate in N,N-dimethyl-formamide

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Takeda Chemical Industries, Ltd.

Patent: US6348485 B1, 2002 ; Title/Abstract

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R.1:2,3-Dihydrobenzofuran-5-carbaldehyde Reference Example 1 2,3-Dihydrobenzofuran-5-carbaldehyde To a solution of 2,3-dihydrobenzofuran (100.0 g, 832 mmols) in N,N-dimethylformamide (134.0 g, 1.83 mols) was added dropwise phosphorus oxychloride (255.1 g, 1.66 mols), then the mixture was stirred at 80-90° C. for 7.5 hours.

The mixture was cooled to room temperature, poured into water (1 L) and stirred for 15 hours.

The product was extracted with toluene (1.5 L).

The extract was washed with water (500 mL) followed by a saturated aqueous solution of sodium bicarbonate (500 mL) and concentrated under reduced pressure to obtain 115.9 g (yield: 94percent) of the title compound.

Multi-step reaction with 2 steps 1: 100 percent / Br2

2: 98 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

Matsunaga, Nobuyuki; Kaku, Tomohiro; Ojida, Akio; Tanaka, Toshimasa; Hara, Takahito; Yamaoka, Masuo; Kusaka, Masami; Tasaka, Akihiro

Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 16 p. 4313 - 4336 Title/Abstract

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7

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Rx-ID: 24199131 Find similar reactions

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in tetrahydrofuran; hexane; water; N,Ndimethyl-formamide

Takeda Chemical Industries, Ltd.

Patent: US6649643 B1, 2003 ;

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Title/Abstract

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19.i:(i) (i) Production of Ethyl 2,3-Dihydronaphtho[2,3-b]furan-6-carboxylate 5-Bromo-2,3-dihydrobenzofuran (38.86 g), which was prepared according to the literature (Alabaster, Ramon J. et al., Synthesis, 1988, vol. 12, pp950.), was dissolved in THF (300 mL) and cooled to -78° C. n-Butyl-lithium

in hexane (1.6M; 160 mL) was added to the solution and stirred for 30 min. DMF (40 mL) was added to the mixture and was allowed to warm to room temperature.

Water was added to the mixture and the solvent was evaporated.

The residue was diluted with ethyl acetate, washed with water and brine, dried and concentrated to give crude product of 5-formyl-2,3-dihydrobenzofuran (28.47 g) as an oil.

8

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Rx-ID: 1638389 Find similar reactions

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92%

With titanium tetrachloride in dichloromethane

Vilsmeier-Haack reaction; 1 h;

Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori

Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4222 - 4239 Title/Abstract

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92%

With titanium chloride in dichloromethane; water

Takeda Chemical Industries, Ltd.

Patent: US6034239 A1, 2000 ;

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Title/Abstract

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R.1:2,3-Dihydrobenzofuran-5-carbaldehyde Reference Example 1 2,3-Dihydrobenzofuran-5-carbaldehyde Titanium chloride (28 ml) was dropwise added to a dichloromethane (100 ml) solution containing 2,3-dihydrobenzofuran (10.0 g, 83.2 mmols) and dichloromethyl methyl ether (11.3 ml, 0.125 mmols), while cooling with ice.

The mixture was stirred for 1 hour, while still cooling with ice, and then water was added thereto.

Dichloromethane was removed under reduced pressure, and the residue was extracted with ethyl acetate.

The extract was washed with a saturated saline solution, then dried with anhydrous magnesium sulfate and concentrated under reduced pressure.

The residue was purified through silica-gel chromatography (hexane/ethyl acetate=1/1) to obtain 11.4 g (yield: 92percent) of the target compound.

This was oily.

NMR (CDCl3) δ: 3.28 (2H, t, J=8.8 Hz), 4.70 (2H, t, J=8.8 Hz), 6.88 (1H, d, J=8.4 Hz), 7.67 (1H, dd, J=1.0 Hz, 8.4 Hz), 7.75 (1H, d, J=1.0 Hz), 9.83 (1H, s) 92%

With titanium tetrachloride in dichloromethane

1 h;

Takeda Chemical Industries, Ltd.

Patent: EP1199304 A1, 2002 ; Location in patent: Referential example 1 ; Title/Abstract

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90%

With tin(IV) chloride in dichloromethane T=0°C; 0.333333 h;

60%

Monte, Aaron P.; Marona-Lewicka, Danuta; Cozzi, Nicholas V.; Nichols, David E.

Journal of Medicinal Chemistry, 1993 , vol. 36, # 23 p. 3700 - 3706 Title/Abstract

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With tin(IV) chloride in dichloromethane

Abbott Laboratories

Patent: US6162927 A1, 2000 ;

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Title/Abstract

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52.A:2,3-Dihydrobenzofuran-5-carboxaldehyde EXAMPLE 52A 2,3-Dihydrobenzofuran-5-carboxaldehyde To a stirred solution of α,α-dichloromethyl methyl ether (2.15 g, 19 mmol, 1.35 eq) in methylene chloride (30 mL) at -40° C. was added successively stannic chloride (1.65 g, 17 mmol, 1.2 eq) and 15 minutes later, a solution of 2,3-dihydrobenzofuran (1.68 g, 14 mmol) in CH2 Cl2 (5 mL) maintaining the temperature at or below -35° C. The mixture was warmed to 0° C., stirred 1 hour, then poured into ice-water, and stirred a further 30 minutes.

The mixture was diluted with ether, and the phases separated.

The organic phase was concentrated in vacuo, and the residue purified by vacuum distillation to yield the title compound (1.25 g, 60percent) as a colorless liquid. b.p. 119-121° C. at 0.3 mm Hg.

60%

With tin(IV) chloride in dichloromethane

Abbott Laboratories

Patent: US5767144 A1, 1998 ;

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Title/Abstract

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Abbott Laboratories

Patent: US5622971 A1, 1997 ; Title/Abstract

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52.A:2,3-Dihydrobenzofuran-5-carboxaldehyde

EXAMPLE 52A 2,3-Dihydrobenzofuran-5-carboxaldehyde To a stirred solution of α,α-dichloromethyl methyl ether (2.15 g, 19 mmol, 1.35 eq) in methylene chloride (30 mL) at -40° C. was added successively stannic chloride (1.65 g, 17 mmol, 1.2 eq) and 15 minutes later, a solution of 2,3-dihydrobenzofuran (1.68 g, 14 mmol) in CH2 Cl2 (5 mL) maintaining the temperature at or below -35° C. The mixture was warmed to 0° C., stirred 1 hour, then poured into ice-water, and stirred a further 30 minutes.

The mixture was diluted with ether, and the phases separated.

The organic phase was concentrated in vacuo, and the residue purified by vacuum distillation to yield the title compound (1.25 g, 60percent) as a colorless liquid. b.p. 119°-121° C. at 0.3 mm Hg.

9

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Rx-ID: 8573403 Find similar reactions

75%

Stage #1: 2,4-dibromo-1-(2-chloroethoxy)-benzene With n-butyllithium in tetrahydrofuran

T=-40°C; Metallation; Stage #2: N,N-dimethyl-formamide in tetrahydrofuran

T=-40 - 20°C; Formylation; Parham cyclization;

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Plotkin, Michael; Chen, Sanyou; Spoors, P. Grant

Tetrahedron Letters, 2000 , vol. 41, # 14 p. 2269 - 2273 Title/Abstract

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10

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Multi-step reaction with 2 steps 1.1: K2CO3 / dimethylformamide 2.1: n-BiLu / tetrahydrofuran / -40 °C 2.2: 75 percent / tetrahydrofuran / -40 20 °C View Scheme

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Rx-ID: 15914396 Find similar reactions

Plotkin, Michael; Chen, Sanyou; Spoors, P. Grant

Tetrahedron Letters, 2000 , vol. 41, # 14 p. 2269 - 2273 Title/Abstract

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11

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58%

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Rx-ID: 24454242 Find similar reactions

Eisai Co., Ltd.

Patent: US5340833 A1, 1994 ; Title/Abstract

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4-[E,Z-2-(2,3-Dihydrobenzo[b]furan-5-yl)ethenyl]benzo[b]thiophene-2-carboxamidine hydrochloride

The bromide (117.9 mg, 0.59 mmol) was treated with 2 equiv. of n-BuLi in THF at -78° C. under N2 followed by DMF to yield 2,3-dihydrobenzofuran-5-carboxaldehyde (51.3 mg, 58percent) after workup and chromatography (12percent EtOAc/hexanes) as a pale yellow syrup.

12

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Rx-ID: 1638388 Find similar reactions

55%

With titanium tetrachloride

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Kelly, David P.; Jenkins, Margot J.

Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 409 - 413 Title/Abstract

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13

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Rx-ID: 73047 Find similar reactions

With hydrogenchloride; aluminium trichloride; benzene

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Baddeley et al.

Journal of the Chemical Society, 1956 , p. 2455,246 Full Text View citing articles Show Details

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