Diethyl Oxalate → 2,4-Dioxo-4-phenyl-butyric acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A stirred solution of acetophenone (5 g, 0.0416 mole), diethyl oxalate (7.23 g, 0.0416 mole) in DMF (40 mL) was cooled to 0° C. for 10 minutes. NaH (60% w/w dispersion in oil) (2.0 g, 0.083 mole) was then added, and the resulting mixture was stirred at the same temperature for 30 minutes, then stirred at ambient temperature for 1 hour. The mixture was then heated at 50° C. for 30 minutes. The reaction mixture was quenched with iced water, acidified with aqueous 2.4N HCl solution and the resulting precipitate was isolated by filtration and dried to afford 3.8 g (42%) of 2,4-dioxo-4-phenyl-butyric acid ethyl ester. LCMS: 221.07 (M+1)+, 85.2%.

Provenance & Evidence