Potassium Carbonate → Methyl E-4-(2-{2-[2-(4-tert-butylbenzyloxy)phenyl]vinyl}-6-cyanohexyl)benzoate

Participants

Reaction Steps

A solution of 2.976 g (8.19 mmol) of methyl E-4-{6-cyano-2-[2-(2-hydroxyphenyl)vinyl]hexyl}-benzoate from Example 119A in 100 ml of dry acetonitrile is mixed with 2.789 g (12.28 mmol) of 4-(tert-butyl)benzyl bromide and 1.697 g (12.28 mmol) of anhydrous potassium carbonate and heated to reflux for 12 hours. The mixture is then filtered and the filtrate is concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The organic phase is concentrated. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 8:1→4:1). 3.85 g (92% yield) of a solid are obtained.

Provenance & Evidence