Sodium Hydroxide → HCID 59117356, compound

Participants

Reaction Steps

A solution of the product from step B (E and Z isomers) (11 g , 32.7 mmol) in MeOH (150 ml) was treated with 2N NaOH (32 ml, 65 mmol) for 3 hours. Methanol was then evaporated and the solution was acidified to pH 5.5 with 6N HCl. The resulting precipitate was filtered and washed with a small quantity of water. The precipitate was taken up in MeOH. The insoluble material was washed with a mixture of MeOH/ether to give after drying 2.3 g of E isomer 3-((E)-2-(4-fluorophenyl)-3-(imidazol-1-yl)-prop-1-enyl)benzoic acid (22%). The above filtrate was evaporated and triturated in ether to give the E isomer 3-((E)-2-(4-fluorophenyl)-3-(imidazol-1-yl)-prop-1-enyl)benzoic acid (7.7 g, 67%) as a solid.

Provenance & Evidence