ethyl 1-benzyl-1H-pyrazole-4-carboxylate → (1-benzyl-1H-pyrazol-4-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of lithium aluminum hydride (LAH) (68 mg, 1.79 mmol) in THF (8 mL) at 0° C. was added dropwise over 5 min a solution of ethyl 1-benzyl-1H-pyrazole-4-carboxylate (250 mg, 1.1 mmol) in THF (5 mL). After stirring for 1 h at 0° C., it was warmed to rt for 30 min and then quenched with 1N HCl until a clear solution was obtained. Extraction with EtOAc (3×50 mL) and washing of the combined organic layers with water, and then brine, provided the crude (1-benzyl-1H-pyrazol-4-yl)methanol after drying and evaporation of the solvent. Crude 1H NMR was clean enough to be used as is without further purification: crude yield 192 mg (94%). 1H NMR (400 MHz, CDCl3) δ ppm 4.58 (s, 2H), 5.29 (s, 2H), 7.21-7.26 (m, 2H), 7.29-7.38 (m, 3H), 7.39 (s, 1H), 7.55 (s, 1H); LCMS-MS (ESI+) 188.90 (M+H).

Provenance & Evidence