Sodium hydride → Diallyl 2-[2-(4-cyanophenyl)ethyl]-2-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)malonate

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Reaction Steps

10 g (31.91 mmol) of diallyl 2-[2-(4-cyanophenyl)ethyl]malonate are dissolved in 250 ml of dioxane and, at 0° C., 1.4 g (35.1 mmol) of 60% sodium hydride are added in portions, and the mixture is stirred at room temperature for 30 min. After renewed cooling to 0° C., a solution of 14.53 g (38.30 mmol) of 3,5-difluoro-4-triisopropylsilanyloxybenzyl bromide in 250 ml of dioxane is added dropwise, and the mixture is stirred while warming to room temperature for 2 h. The reaction solution is then added to 500 ml of saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1). 14.3 g (73% of theory) of the title compound are obtained.

Provenance & Evidence