Water → HCID 70544649, compound

Participants

Reaction Steps

Sodium hydride (1.81 g of 50% dispersion in mineral oil) was added in portions to a stirred solution of 3-hydroxy-2-(1-imidazolylmethyl)pyridine (6.00 g) in dry N,N-dimethylformamide (100 ml) at 0° C. The mixture was stirred for 15 minutes and a solution of ethyl 4-bromomethyl-benzoate (8.34 g) in dry N,N-dimethylformamide (20 ml) was then added over a period of 10 minutes. The mixture was allowed to warm to room temperature, stirred for 4 hours and water (5 ml) was then added. The solution was evaporated and the residue chromatographed on silica gel, eluting with chloroform. The product-containing fractions were combined and evaporated to give an oil which solidified on trituration with diethyl ether. Recrystallization from diethyl ether gave 3-(4-ethoxycarbonylbenzyloxy)-2-(1-imidazolylmethyl)pyridine (4.85 g), m.p. 100°-101° C.

Provenance & Evidence