Hydrochloric Acid → Ethyl 4-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-2,4-dioxobutanoate

Participants

Reaction Steps

To a stirred solution of 1-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]ethanone (5.1 g, 11 mmol) in THF (50 mL) was added drop wise 1M lithium (bis trimethylsilylamide/THF solution (12 mL, 12 mmol) at −50° C. After 30 minutes, a solution of diethyl oxalate (1.7 mL) in THF (15 mL) was slowly added and the stirring was continued for 1 hours. The solution was taken up in brine (200 mL) and treated with 1 M HCl solution (13 mL), then extracted with ethyl acetate. The organic phase was dried and the solvent removed. The crude was filtered on a small pad of silica gel eluting with hexane/ethyl acetate 2/1 to afford the title compound (5.7 g, 75% yield).

Provenance & Evidence