Dimethyl oxalate → HCID 69477228, compound

Participants

Reaction Steps

NaH (60% dispersion, 2.22 g, 55.5 mmol) was added to a solution of dimethyl oxalate (2.73 g, 23.1 mmol) and 1,1-dimethylethyl(4-acetylphenyl)carbamate (N-BOC-4-aminoacetophenone, 5.44 g, 23.1 mmol) in anhydrous DMF (50 mL) at 0° C. The reaction mixture was allowed to warm to room temperature overnight and quenched with saturated aqueous NH4Cl and neutralized with 1M HCl. The reaction was diluted with ethyl acetate (80 mL) and the organic layer washed successively with saturated aqueous NaHCO3 and brine. The organic phase was separated and dried over Na2SO4, filtered, concentrated in vacuo and triturated with chloroform to provide the condensation product (3.77 g, 53.1% yield).

Provenance & Evidence