Triethylamine → z-1-{4-[2-(2-Benzyloxyethoxy)ethoxy]phenyl}-4-chloro-1,2-diphenyl-but-1-ene

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Reaction Conditions

Reaction Steps

1-{4-[2-(2-Benzyloxy-ethoxy)ethoxy]phenyl}-1,2-diphenyl-butane-1,4-diol (10.0 g, 19.5 mmol) is dissolved in toluene (50 ml). Triethylamine (2.17 g, 21.4 mmol) is added to the solution and the mixture is cooled to −10° C. Thionyl chloride (6.9 g, 58.5 mmol) is added to the mixture at −10-±0° C. The mixture is stirred for 1 hour at 0-5° C., warmed up to 70° C. and stirred at this temperature for 4 hours. Solvent is evaporated, the residue is dissolved to toluene, washed three times with 1M HCl solution and twice with water. The Z-isomer of the product is crystallized from isopropanol-ethyl acetate. Yield 3.0 g. The filtrate is purified by flash chromatography to give E-isomer.

Provenance & Evidence