Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 68786094, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-methoxy-4-trifluoromethyl-3-pyridinecarboxaldehyde (150 mg, 0.73 mmol) in toluene (8 mL) was added methyl(triphenylphosphoranylidene)acetate (270 mg, 0.81 mmol). The mixture was heated at 110° C. for overnight, cooled to room temperature, and diluted with EtOAc and water. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc/hexanes=1/4) to give 3-(6-methoxy-4-trifluoromethylpyridin-3-yl)-acrylic acid methyl ester (140 mg, 73.3%) as a mixture of cis- and trans-isomers (cis-/trans-=1/10). The trans-isomer was then isolated by recrystallization from hexanes to give 60 mg as a solid.

Provenance & Evidence