Diethyl Oxalate → Ethyl 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutanoate

Participants

Reaction Conditions

Reaction Steps

A 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (30 mL, 30 mmol) in anhydrous diethyl ether (120 mL) under argon was cooled to −78° C. in a dry ice/acetone bath. A solution of 4-chloropropiophenone (5.0 g, 29.7 mmol) in anhydrous ether (24 mL) was added dropwise and the mixture was stirred an additional 45 minutes at −78° C. Diethyl oxalate (4.6 mL, 33.9 mmol) was added in one portion; the reaction was warmed to room temperature, and stirred overnight. The light yellow precipitate that formed was collected, washed with ether and dried under vacuum to obtain the lithium enolate of ethyl 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutanoate (2.75 g, 10.0 mmol).

Provenance & Evidence