Hydrochloric Acid → [5-(5-Methyl-tetrazol-1-yl)-benzofuran-7-yl]-methanol

Participants

Reaction Steps

A solution of 1-(7-hydroxymethyl-benzofuran-5-yl)-ethanone (250 mg,) and sodium azide (0.68 g) in acetonitrile (40 ml) was treated with titanium tetrachloride (0.29 ml) and heated at reflux for 1.5 h. The reaction mixture was allowed to cool, treated with 2N hydrochloric acid (40 ml) and extracted with ethyl acetate (2×40 ml). The organic phases were dried, combined, filtered and the filtrate evaporated in vacuo to give a yellow oil. Purification by FCC eluted with hexane:ethyl acetate (1:3) gave the title compound as a clear gum (131 mg).

Provenance & Evidence