2-Pyridinecarboxaldehyde → Methyl 3-(2-pyridyl)-2-propenoate

Participants

Reaction Steps

To a solution of methyl triphenylphosphoranylideneacetate (31.2 g) in CH2Cl2 (120 mL) was added dropwise over 15 minutes 2-pyridine carboxaldehyde (8.9 mL, 0.093 mol) in CH2Cl2 (40 mL). The mixture was heated to reflux for 8 hours, additional ylide (3.1 g) was added and the mixture was refluxed overnight. The reaction mixture was cooled, concentrated to 1/2 value and allowed to stand for 2 hours. A solid was collected by filtration and was washed with CH2Cl2 /hexane. The filtrate was concentrated in vacuo and the residue was vacuum distilled at 80°-107° C. and 1.5 mm Hg to afford 12.2 g (80%) of methyl 3-(2-pyridyl)-2-propenoate.

Provenance & Evidence