Lithium hydroxide, monohydrate → 3-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-5-(trifluoromethyl)benzamide

Participants

Reaction Conditions

Reaction Steps

A solution of {1-[3-cyano-5-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl acetate (Intermediate 30, 3.33 g) in methanol (10.0 mL), tetrahydrofuran (20 mL) and water (10.0 mL) was cooled in an ice-water bath before the addition of lithium hydroxide monohydrate (0.449 g, 10.7 mmol). The reaction was stirred at 0-5° C. for 2 hours. The reaction was diluted with water (30 mL) and the organic solvent removed under vacuum. The suspension was extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried and the solvent removed to yield a white solid. The solid was triturated with diethyl ether (2×25 mL), the solvent decanted and the residue dried under vacuum to yield the intermediate 3-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-5-(trifluoromethyl)benzamide as a white solid (1.37 g).

Provenance & Evidence