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1
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50%
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Stage #1: benzeneacetic acid methyl ester With lithium hexamethyldisilazane in tetrahydrofuran
T=-78°C; 0.333333 h; Stage #2: acetic anhydride in tetrahydrofuran
T=-78 - 0°C; Hide Experimental Procedure
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CARDIOXYL PHARMACEUTICALS, INC.; THE JOHNS HOPKINS UNIVERSITY; KALISH, Vincent, J.; BROOKFIELD, Frederick, A.; COURTNEY, Stephen, M.; FROST, Lisa, M.; TOSCANO, John, P.; GUTHRIE, Daryl, A.; NORTH, Carl, L.
Patent: WO2015/183839 A1, 2015 ; Location in patent: Page/Page column 184; 185; 193; 194; 219 ; Title/Abstract Full Text Show Details
6.1; 24.1:6.1 Methyl 3-oxo-2-phenylbutanoate
General procedure: General Method 13: Phenylbutanoate Synthesis:_To a solution of an alkyl phenyl acetate (1 equiv) in THF (10 vol) in a flask at a temperature of about -78°C (dry ice-acetone bath) was added 1M lithium 1,1,1,3,3,3-hexamethyldisilazan-2-ide in THF (2 equiv). The reaction mixture was stirred for about 20 minutes at about -78°C. Acetic anhydride (1 equiv) was added rapidly, the flask was removed from the dry ice-acetone bath and placedinto an ice-water bath where it was allowed to warm to about 0°C, and stirred until substantially complete consumption of the starting material was achieved as determined by LC-MS. The mixture was quenched with ammonium chloride solution (10 vol) and the product was extracted into ethyl acetate (3 x 10 vol). The ethyl acetate layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a product which was chromatographed by silica gelcolumn chromatography eluting with 0-100percent ethyl acetate:heptanes gradients.:_Methyl 3 -oxo-2-phenylbutanoate was synthesized from methyl 2 -phenylacetate according to General Method 13 and was chromatographed by silica gel column chromatography (12percent ethyl acetate in heptanes) to provide the title compound as a pale yellow oil (22 g, 50percent yield). LC-MS:tR—l.13/l.16 mi [M+H] =193.