Imidazole → 5-(2-Iodo-ethyl)-2-pentyl-benzoxazole

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, a 0° C. solution of 2-(2-pentyl-benzoxazol-5-yl)-ethanol (1.63 g, 6.99 mmol) in dry THF (49 ml) was treated with triphenyl phosphine (2.018 b, 7.693 mmol) and imidazole (1.05 g, 15.38 mmol). After complete dissolution iodide (1.95 g, 7.69 mmol) was added in small portion so that the reaction temperature never exceeded 4° C. After stirring for 3 hours at 0° C. the reaction mixture was distributed between diethyl ether and saturated aqueous ammonium hydrochloride. The organic layer was evaporated in vacuum, suspended in diethyl ether, filtered and the filtrate concentrated in vacuum. Silica gel chromatography (eluent: pentane/diethyl ether 4/1) followed by crystallization from pentane provided the title compound as colorless crystals. mp: 47.7/48.7° C.

Provenance & Evidence