Dimethylformamide → (S)-4-benzyl-3-[(2E)-3-(4-chlorophenyl)prop-2-enoyl]-1,3-oxazolidin-2-one

Participants

Reaction Steps

A solution of oxalyl chloride (10.82 mL, 124 mmol) in dichloromethane (50 mL) was added dropwise to a cooled solution of (2E)-3-(4-chlorophenyl)acrylic acid (11.33 g, 62.0 mmol) in dichloromethane (110 mL) and N,N-dimethylformamide (0.4 μL, 0.01 mmol). After stirring the reaction mixture for 24 hours, the solution was added dropwise to a cooled solution of (4S)-4-benzyl-1,3-oxazolidin-2-one (9.49 g, 53.6 mmol), triethylamine (39.2 mL, 282 mmol) and lithium chloride (11.95 g, 282 mmol) in dichloromethane (110 mL). The reaction mixture was slowly warmed to room temperature, stirred for 2 hours and then water (50 mL) was added. The mixture was diluted with dichloromethane (100 mL) and 5% citric acid solution (2×150 mL) was added. The phases were separated and the organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by column chromatography on silica gel using dichloromethane as eluent afforded the desired product as a white solid, 14.6 g (74%).

Provenance & Evidence