Ammonium Chloride → Methyl 3-[2-(thiazol-2-yl)-3-(imidazol-1-yl)prop-1-en-1-yl]-5-phenylbenzoate

Participants

Reaction Steps

Potassium tert-butoxide (1.05 g; 9.39 mmnol) was added to mixture of thiazol-2-yl imidazol-1-ylmethyl ketone (1.20 g; 6.25 mmol), 3-methoxycarbonyl-5-phenylbenzyl triphenyl phosphonium bromide (5.3 g; 9.39 mmol) and 18-crown-6 (0.08 g; 0.24 mmol) in dichloromethane (20 ml), at −60° C. under an argon atmosphere. After stirring overnight, at room temperature, the resulting mixture was treated with a saturated aqueous solution of ammonium chloride purified by flash chromatography eluting with dichloromethane/ethanol (95/5) to give methyl 3-[2-(thiazol-2-yl)-3-(imidazol-1-yl)prop-1-en-1-yl]-5-phenylbenzoate (Z isomer). Yield=39%.

Provenance & Evidence