3,5-Difluorobenzaldehyde → HCID 14861157, compound

Participants

Reaction Steps

A well stirred solution of 3,5-difluorobenzaldehyde (1.92 g, 13.5 mmol) and methyl benzyloxycarbonylamino-(dimethoxyphosphoryl)acetate (5.37 g, 16.2 mmol) in dry THF (20 mL), under N2, was cooled to 0° C. and 1,1,3,3-tetramethylgaunidine (1.38 g, 16.2 mmol) added via syringe. The reaction was allowed to warm to rt and stir for 6 h, quenched with saturated ammonium chloride and extracted with ethyl acetate. After concentration, the residue was chromatographed on silica gel (elution with 20% ethyl acetate/heptane) to give methyl (Z)-2-benzyloxycarbonylamino-3-phenyl-acrylate (3.55 g) as a white solid. MS (ESI+) for C18H15F2NO4 m/z 348.2 (M+H)+.

Provenance & Evidence