Triphenylphosphine → Methyl 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoate

Participants

Reaction Steps

A mixture of methyl 2-(4-fluorophenethyl)-5-hydroxybenzoate (1.83 g, 6.7 mmol), 2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethanol (1.40 g, 6.68 mmol) and triphenylphosphine (2.10 g, 8.0 mmol) in tetrahydrofuran (25 ml) was stirred at ambient temperature under a nitrogen atmosphere. DEAD (1.39 g, 1.25 ml 8.0 mmol) was added dropwise to the solution. (The reaction was maintained at ambient temperature ±2° C.). The orange solution was then stirred at ambient temperature under a nitrogen atmosphere for 16 hours. The tetrahydrofiran solution was evaporated to dryness to give an oil. Purification by flash column chromatography eluting with ethyl acetate, ethyl acetate/methanol (9:1 and 4:1) gave methyl 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoate (2.07 g, 67%) as a clear oil.

Provenance & Evidence