Diethyl Carbonate → Ethyl 3-(3-cyanophenyl)-3-oxopropanoate

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% dispersion in oil, 8.27 g, 207 mmol, 3.00 equiv) was added to a solution of 3-acetylbenzonitrile (10.0 g, 68.9 mmol, 1 equiv) in tetrahydrofuran (300 mL). The reaction mixture was stirred at 60° C., and a solution of diethyl carbonate (12.5 mL, 103 mmol, 1.50 equiv) in tetrahydrofuran (60 mL) was added over 45 minutes. The light orange reaction mixture was stirred at 60° C. for an additional 2 h, then was cooled to 22° C. Saturated aqueous ammonium chloride solution was added, and the mixture was concentrated to ˜½ volume by rotary evaporation. The resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, and the washed solution was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated to afford ethyl 3-(3-cyanophenyl)-3-oxopropanoate (15 g, 100%) as a white solid. The crude reaction product was taken into the next step without further purification. Calcd (M+1)+: 218.1. Found: 218.0.

Provenance & Evidence