Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 3-(6-Bromopyridin-3-yl)acrylic acid methyl ester

Participants

Reaction Steps

20 g (59.8 mmol) of 2-(triphenylphosphoranylidene)acetic acid methyl ester were added, by portion, to a solution of 11.1 g (59.8 mmol) of 6-bromopyridine-3-carbaldehyde in anhydrous THF at 0° C. The mixture was stirred at 0° C. to room temperature for 4 h. The solvent was removed in vacuo and the residue was purified by chromatography (silica gel, cyclohexane/ethyl acetate 95:5) to give 13.1 g (90.4%) of the title compound (trans/cis ratio 95:5) as a white solid.

Provenance & Evidence