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

Participants

Reaction Steps

The title compound was prepared in the same manner as intermediate 29 using sodium metal (0.168 g, 7.32 mmol), 1-[4-(methyloxy)phenyl]ethanone (1 g, 6.66 mmol), and diethyl ethanedioate (0.903 mL, 6.66 mmol). The crude product was purified using column chromatography (0 to 100% EtOAc/hexanes) to give 0.95 g of product (57%). LCMS E-S (M+H)=250.9. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.43 (m, 3H), 3.91 (s, 3H), 4.41 (q, J=6.65 Hz, 2H), 6.94-7.12 (m, 3H), 8.01 (d, J=8.59 Hz, 2H).

Provenance & Evidence