Triethylamine → 4-(4-(4-Chlorophenyl)-2-oxo-2,5-dihydrofuran-3-yl)benzonitrile

Participants

Reaction Steps

To a stirred and cooled (−15° to −10° C.) solution of 2-(4-cyanophenyl)acetic acid (35 g, 217.18 mmol) in DMF (250 mL) was added potassium t-butoxide (95%, 25.66 g, 217.22 mmol) under argon in small portions keeping the temperature below −10° C. After the addition was complete a solution of 2-bromo-1-(4-chlorophenyl)ethanone (50.71 g, 217.18 mmol) in DMF (75 mL) was added slowly over 30 min. The reaction mixture was stirred for 1 hr keeping the temperature between −10° to 0° C. Et3N (12.0 mL, 86.1 mmol) was added at 0° C. and the reaction mixture was allowed to warm to room temperature over 1.5 hr. Then EtOH (70 mL) was added at room temperature and the reaction mixture was stirred for 10 min. The reaction mixture was cooled in an ice bath and water (300 mL) was added slowly. The light green precipitate formed was collected by filtration, washed thoroughly with water followed by hexanes. The solid thus obtained was dried in a vacuum oven overnight at 50° C. to obtain 4-(4-(4-chlorophenyl)-2-oxo-2,5-dihydrofuran-3-yl)benzonitrile (58.2 g, 91% yield) as a light green solid.

Provenance & Evidence