3-(Chloromethyl)pyridine hydrochloride → HCID 54223650, compound

Participants

Reaction Steps

Sodium (0.37 g.) was dissolved in methanol (70 ml.) and 7-hydroxybenzofuran-2-carboxylic acid methyl ester (1.54 g.) was added. The solution was stirred for 15 minutes and then 3-chloromethylpyridine hydrochloride (1.32 g.) was added. The mixture was heated under reflux for 8 hours and then evaporated. Water was added to the residue and the mixture was extracted several times with ethyl acetate. The combined extracts were washed with water and dried (Na2SO4). Evaporation of the solvent gave a solid which was chromatographed on silica gel. Elution with chloroform gave a solid which was crystallized from methanol/water to give 7-(3-pyridylmethoxy)-benzofuran-2-carboxylic acid methyl ester (1.0 g.), m.p. 117°-118° C.

Provenance & Evidence