Sodium hydride → methyl 4-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]benzoate

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Reaction Steps

To a solution of 3,5-di-tert-butyl-1H-pyrazole (1.00 g, 5.55 mmol) in N,N-dimethylformamide (15 mL) was added sodium hydride (60% in oil, 0.27 g, 6.8 mmol) under ice-cooling. After completion of hydrogen generation, methyl 4-(bromomethyl)benzoate (1.40 g, 6.11 mmol) was added, and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed with water, and dried to give the title compound (1.78 g, yield 98%) as colorless crystals.

Provenance & Evidence