Acetic Acid → Ethyl 3-(pyridin-2-yl)acrylate

Participants

Reaction Steps

To a suspension of sodium hydride (60% in oil, 0.88 g, 22 mmol) in THF (20 ml) was added ethyl diethylphosphonoacetate (4.93 g, 22 mmol) dropwise while ice cooling and the mixture was further stirred at room temperature for 15 minutes and again ice cooled. To the ice cooled mixture was added dropwise a solution of picolinaldehyde (2.14 g, 20 mmol) in THF (10 ml). After the addition, the reaction mixture was heated at 60° C. for 1 hour. Thereafter, the reaction was stopped by treating with 1M aqueous acetic acid. The mixture was diluted with water, and extracted with methylene chloride. The organic layer was treated according to conventional techniques. Evaporation of the solvent yielded a residue which was subjected to recrystallization from hexane to afford ethyl 3-(pyridin-2-yl)-acrylate, yield: 80%.

Provenance & Evidence