Ammonium Chloride → 4-[(4E)-3-{3,5-difluoro-4-[(triisopropylsilyl)oxy]benzyl}-5-(2-hydroxyphenyl)pent-4-en-1-yl]benzonitrile

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Reaction Conditions

Reaction Steps

1.82 ml (2.91 mmol) of a 1.6 M solution of n-butyllithium in hexane are slowly added to a solution of 579 mg (1.25 mmol) of (2-hydroxybenzyl)triphenylphosphonium bromide in 11.5 ml of THF at 0° C. Then, at this temperature, 490 mg (1.04 mmol) of 4-[3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-4-oxobutyl]benzonitrile are slowly metered in. The reaction solution is stirred at 0° C. for 2 h and then mixed with 100 ml of saturated ammonium chloride solution and extracted with diethyl ether. The combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is concentrated to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 379.7 mg (54% of theory) of a colorless solid are obtained.

Provenance & Evidence