Trityl chloride → Ethyl 5-methyl-1-(triphenylmethyl)imidazole-4-carboxylate

Participants

Reaction Steps

Ethyl 5-methyl-4-1H-imidazolecarboxylate (6.16 g) in toluene (100 ml), triphenylmethyl chloride (11.12 g) and triethylamine (5.6 ml) were heated at reflux for 18 h. Toluene was removed under reduced pressure and the residue was dissolved in dichloromethane (100 ml), washed with water (4×50 ml) dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica using 1% methanol in dichloromethane as eluant with a trace of triethylamine. This afforded the title compound (11 g), m.p. 188°-190° C. δH (250 MHz, CDCl3) 1.38-1.42 (3 H, t, J=6.5 Hz, CH3), 1.86 (3 H, s, CH3), 4.36-4.40 (2 H, q, J=7.2 Hz, CH2), 7.10-7.46 (16 H, m, ArH); m/z (NoM+), 243 (Ph3C+, 100%).

Provenance & Evidence