Ethanol → Ethyl pyridine-4-acetate

Participants

Reaction Steps

Thionyl chloride (1.70 ml, 23.0 mmol) was added to a solution of pyridin-4-yl-acetic acid hydrochloride (2.00 g, 11.5 mmol) in EtOH (30 ml) at 0° C. The reaction mixture was heated to reflux for 18 h, then the temperature of the reaction mixture was brought down to room temperature and the volatiles were evaporated in vacuo. The crude reaction mixture was basified with aqueous sodium bicarbonate solution, extracted with ethyl acetate (2×50 ml), washed with water, brine and dried over anhydrous sodium sulfate. After filtration the organic solvent was evaporated and dried to afford 1.50 g (86.2%) of ethyl 2-(pyridin-4-yl)acetate as pale yellow liquid. This was taken as such for the next step.

Provenance & Evidence