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

Participants

Reaction Steps

To a stirred solution of methyl imidazol-4-ylacetate hydrochloride from Step A (4.30 g, 24.3 mmol) in dry DMF (50 mL) under argon were added triethylamine (5.41 g, 53.5 mmol) and triphenylmethyl bromide (8.64 g, 26.7 mmol). The reaction mixture was stirred at ambient temperature overnight, then partitioned between water (250 mL) and EtOAc (250 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with 50% hexane in EtOAc to remove nonpolar impurities, then EtOAc to elute the titled product as a white solid.

Provenance & Evidence