Acetic Acid → HCID 178478030, compound

Participants

Reaction Steps

To a stirred mixture of 4-[2-(2-chloro-phenyl)-vinyl]-1-trityl-1H-imidazole (329 mg) at r.t. in ethanol (7 ml) and chloroform (3 ml) under an argon atmosphere were added acetic acid (0.2 ml) and 10% Pd/C (30 mg). The mixture was hydrogenated (ambient pressure) over night. The catalyst was filtered off and washed with ethanol. The mixture was concentrated to leave a light brown gum. This material was taken up in ethanol (3 ml) and 2 N HCl (3 ml) and heated to reflux for 3 h. Then, the mixture was cooled to r.t., concentrated. The residual solid was taken up in 1 N NaOH (10 ml) and extracted with CH2Cl2/MeOH 4:1. The combined organics were dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2→CH2Cl2/MeOH 9:1) to give 4-[2-(2-chloro-phenyl)-ethyl]-1H-imidazole (44 mg) as light brown gum. MS (ISP): 207.1 ([M+H]+)

Provenance & Evidence