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

Participants

Reaction Steps

Sodium metal (0.143 g, 6.21 mmol) was dissolved into ethanol (3 mL) and the resulting solution was cooled with an ice bath. A mixture of 1-(4-chlorophenyl)ethanone (0.756 mL, 5.65 mmol) and diethyl ethanedioate (0.766 mL, 5.65 mmol) were added dropwise, and the reaction mixture was stirred for 16 h. The reaction mixture was quenched with ice water (5 mL) and acidified to ˜pH 3 with 1N HCl. The precipitate was collected by filtration and dried under high vacuum to give 1.39 g (97%) of product. LCMS E-S (M+H)=255.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.29 (m, 3H), 4.27 (d, J=6.57 Hz, 2H), 7.60 (d, J=7.58 Hz, 2H), 8.02 (d, J=6.57 Hz, 2H).

Provenance & Evidence