Imidazole → HCID 53725360, compound

Participants

Reaction Steps

A mixture of imidazole (0.25 g, 3.67 mmol), potassium tert-butoxide (0.42 g, 3.75 mmol), ethyl 3-(3-bromo-4-bromomethylphenyl)prop-2-enoate (1.29 g, 3.7 mmol) and 18-crown-6 (0.1 g) in dry ether was stirred at room temperature for 72 h. Water (5 ml) was then added, and the aqueous layer was extracted with ether (3×50 ml). The ether solutions were combined, dried (MgSO4) and then concentrated to afford a pale yellow oil. The oil was `flash` chromatographed using chloroform/methanol 9:1 as eluant. The product fractions were combined, dried (MgSO4) and concentrated to afford ethyl 3-[3-bromo-4-(imidazol-1-ylmethyl)phenyl]prop-2-enoate as a white solid. NMR data was consistent with the assigned structure.

Provenance & Evidence