Dimethyl oxalate → Dimethyl 2-(benzyloxy)-3-oxosuccinate

Participants

Reaction Steps

A solution of methyl(benzyloxy)acetate (1 eq) and dimethyl oxalate (1.2 eq) in dry THF was cooled to −78° C. and LDA (2M in THF-heptane, 1.2 eq) was added dropwise. After stirring for an hour the cold bath was removed, and stirring was continued for an additional hour. The reaction was quenched at 0° C. by pouring into cold 1N aq HCl, and the aqueous phase was extracted with EtOAc; the organic layer was washed with brine, dried and concentrated to give a crude that was used without further purification.

Provenance & Evidence