Ammonium Chloride → 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrile

Participants

Reaction Steps

A solution of p-toluenesufonylmethylisocyanide (10.3 g) in dimethoxyethane (50 ml) was added to a mixture of potassium t-butoxide (11.2 g) and dimethoxyethane (50 ml) at −78° C., and the mixture was stirred for 5 minutes. A solution of 1-benzyl-3-benzyloxy-1H-pyrazole-4-carbaldehyde (14.6 g) in dimethoxyethane (50 ml) was added to the mixture. After stirring at the same temperature for 1 hour, the mixture was stirred for 1 hour while raising the temperature. Methanol (150 ml) was added to the mixture, which was refluxed for 1 hour. After cooling, the reaction solution was poured into saturated aqueous ammonium chloride solution, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrile (13.1 g, yield 86%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio).

Provenance & Evidence