Triphenylphosphine Oxide → (E)-Methyl 3-[3-(phenylmethoxy)pyridin-2-yl]-2-propenoate

Participants

Reaction Steps

Crude 3-(phenylmethoxy)-2-pyridinecarboxaldehyde (30 g) and carbomethoxymethylenetriphenylphosphorane (55 g) in acetonitrile (800 ml) were stirred at reflux overnight. The solution was evaporated onto silica (Merck 9385) which was then purified by FCC eluting with ethyl acetate to give the product contaminated with triphenylphosphine oxide. This crude product was triturated with ether and the triturate was evaporated to an oil which was chromatographed on a column of silica (Merck 9385) eluting with cyclohexane followed by cyclohexane/ethyl acetate (4:1) to give the title compound as a yellow oil (270 g), t.l.c. (cyclohexane/ethyl acetate/triethylamine 80:20:1) Rf 0.17.

Provenance & Evidence