Water → 5-(Benzyloxy)-2-chloropyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 12.9 g (0.1 mol) of 5-hydroxy-2-chloropyridine in 50 ml of dimethylformamide is added to a suspension of 4.8 g (0.1 mol) of sodium hydride (a 50% dispersion in mineral oil; washed with toluene) in 100 ml of dimethylformamide. The mixture is stirred until the evolution of hydrogen has ceased and then, after cooling with the aid of an ice-bath, 12.6 g (0.1 mol, 11.5 cc) of benzyl chloride are introduced dropwise. The mixture is heated at 60° C. for one hour, left to stand overnight and then poured into iced water, and extraction is carried out with diethyl ether. The ether phase is washed with water, dried and filtered and the filtrate is evaporated. The product, i.e. 2-chloro-5-benzyloxypyridine, is distilled. Its boiling point (0.1 mm Hg) is 135° C.

Provenance & Evidence