Water → N-[3-(1-Hydroxyhexyl)phenyl]pyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

The aldehyde (1.1 g) was dissolved in dry tetrahydrofuran, and cooled in an ice bath. To this cold solution was added dropwise, a solution of pentylmagnesium bromide (prepared from 1-bromopentane (1.9 g) and magnesium turnings (0.31 g) in dry ether). The reaction mixture was stirred at 0° C. for two hours, allowed to warm to room temperature and was carefully poured into cold water. The aqueous solution was extracted with ethyl acetate, and the organic extract was washed with aqueous ammonium chloride solution, brine and then dried over anhydrous magnesium sulfate. All volatilss were removed to leave a viscous liquid which quickly solidified on standing. This solid was crystallized from ethyl acetate/hexane to give pure product.

Provenance & Evidence