Water → 1-(4-Pyridyl)-3-buten-1-ol

Participants

Reaction Conditions

Reaction Steps

4.75 g (50 mmol) of pyridine-4-carboxaldehyde was dissolved in 50 ml THF and cooled to 0° C. Allyl lithium was then added with stirring until the mixture turned the dark color characteristic of the allyl lithium solution. After stirring for an additional 5 minutes, water was slowly added at 0° C. until two phases formed and all precipitate was dissolved. The THF layer was separated, dried over MgSO4, and evaporated in vacuo to an oil. Flash chromatography yielded 4.69 g (63%) of product as an oil. 1H NMR (CDCL3): 8.5 and 7.3 (4H, pyridyl), 5.8 and 5.15 (3H, vinyl), 4.75 (1H, CHOH), 3.6 (1H, OH), and 2.5 (2H, CH2) ppm.

Provenance & Evidence