Potassium Carbonate → E-4-[5-[2-(4-tert-Butylbenzyloxy)phenyl]-3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)pent-4-enyl]benzonitrile

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Reaction Steps

1.7 g (3 mmol) of 4-[(4E)-3-{3,5-difluoro-4-[(triisopropylsilyl)oxy]benzyl}-5-(2-hydroxyphenyl)pent-4-en-1-yl]benzonitrile in 35 ml of acetonitrile are mixed with 627 mg (4.5 mmol) of potassium carbonate and 1 g (4.5 mmol) of 4-tert-butylbenzyl bromide and stirred under reflux for 12 hours. The solvent is stripped off in vacuo, and the residue is taken up in ethyl acetate. The organic phase is washed once with sodium bicarbonate solution and once with sodium chloride solution, dried over sodium sulfate and concentrated. The crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 628 mg (85% purity, 0.76 mmol, 25% of theory) of the title compound are obtained.

Provenance & Evidence