Ammonium Chloride → 4-[Hydroxy(4-methoxyphenyl)methyl]benzonitrile

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Reaction Steps

To a suspension of 4-(4-methoxybenzoyl)benzonitrile 26-1 (J. Med. Chem. 1991, 34, 2768-2778) (0.783 g, 3.3 mmol) in ethanol (35 ml) under nitrogen cooled in an ice-bath was added sodium borohydride (0.250 g, 6.6 mmol). The mixture was stirred 4 h with ice-bath cooling. To the resulting solution was added saturated ammonium chloride solution (35 ml). The mixture was partially evaporated under reduced pressure, and the resulting aqueous mixture was extracted with ethyl acetate (2×100 ml). The combined organic fractions were washed with brine (50 ml), dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/hexane (1:6 increasing to 1:3), to give product 26-2 as an oil.

Provenance & Evidence