4-chloro-1-methyl-1H-pyrazole-3-carbaldehyde → (4-chloro-1-methyl-1H-pyrazol-3-yl)methanol

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Reaction Steps

To a solution of sodium borohydride (393 mg, 10.4 mmol) in methanol (25 mL) was added a solution of 4-chloro-1-methyl-1H-pyrazole-3-carbaldehyde (1.0 g, 6.9 mmol) in methanol (10 mL) at 0° C. The mixture was stirred for 4 hours at room temperature. The solvent was evaporated, water was added, and the mixture was extracted 3 times with ethyl acetate. The combined organic phases were washed with brine and dried over sodium sulfate. After evaporation of the solvent, (4-chloro-1-methyl-1H-pyrazol-3-yl)methanol was obtained as a yellow oil (680 mg, 67% yield) and used in the next step without further purification; 1H NMR (400 MHz, DMSO-d6): δ 3.77 (s, 3H), 4.34 (d, J=5.6 Hz, 2H), 5.03 (s, J=5.6 Hz, 1H), 7.85 (s, 1H).

Provenance & Evidence