Diisobutylaluminum hydride → (2-(2,6-Dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl)methanol

Participants

Reaction Steps

To a solution of methyl 2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylate (0.35 g, 1.24 mmol) in DCM (20 mL), DiBAL-H (1 M solution in toluene, 4.98 mL, 4.98 mmol) is added drop wise at 0° C. The reaction mixture is warmed to room temperature and stirred for 2 hours. The reaction is quenched with aqueous NH4Cl solution and extracted with EtOAc (4×50 mL). The combined extracts are dried over sodium sulphate, filtered, and concentrated. The crude material is purified by silica gel chromatography (combiflash) eluting with 50% EtOAc in hexanes. The product is concentrated to give the title compound as a transparent liquid (0.18 g, 57%). LCMS m/z 254 (M+H)+.

Provenance & Evidence