Water → Ethyl E-6-[2-(4-cyanophenyl)ethyl]-8-(2-hydroxyphenyl)oct-7-enoate

Participants

Reaction Steps

15.91 ml (25.45 mmol) of a 1.6 M solution of n-butyllithium in hexane are slowly added to a solution of 5.066 g (10.91 mmol) of (2-hydroxybenzyl)triphenylphosphonium bromide in 38 ml of anhydrous THF at 0° C. Then, at this temperature, 2.740 g (9.09 mmol) of ethyl 8-(4-cyanophenyl)-6-formyloctanoate from Example 86A, dissolved in 38 ml of THF, are slowly metered in. After the reaction solution has been warmed to room temperature it is stirred for 12 hours and, after addition of some water, concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and 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→4:1). 2.30 g (5.88 mmol, 63% yield) of a colorless solid are obtained.

Provenance & Evidence