Triethylamine → 1-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

Participants

Reaction Steps

To a solution of 1H-imidazole-4-acetic acid methyl ester hydrochloride (24.85 g, 0.141 mol) in DMF (115 mL) was added triethylamine (57.2 mL, 0.412 mol) and triphenylmethyl bromide (55.3 g, 0.171 mol) and the suspension was stirred for 24 h. After this time, the reaction mixture was diluted with EtOAc (1 L) and water (350 mL). The organic phase was washed with sat. aqueous NaHCO3 (350 mL), dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (SiO2, 0-100% ethyl acetate in hexanes; gradient elution) to provide the title compound as a white solid.

Provenance & Evidence