Diisobutylaluminum hydride → (1-(2,6-dichlorophenyl)-4-isopropyl-1H-1,2,3-triazol-5-yl)methanol

Participants

Reaction Steps

To a 0° C. solution of 3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester (2.88 g) in THF (25 mL) is added 1 M DIBAL in toluene (38 mL). The reaction is allowed to warm to room temperature. Upon completion, the reaction mixture is quenched slowly with water and is acidified with 1 N HCl. The resulting solution is extracted two times with ethyl acetate. The combined organic layers are washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (2.26 g). ES/MS (m/e) 284 (M+0), 286 (M+2); mp: 154-155° C.

Provenance & Evidence