Reaction #7214

Reaction equation

4,5-diphenyl-1H-imidazole

NaH

SEMCl

→

title compound

Yield 64.0%

4,5-Diphenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole

Yield 64.0%

Conditions

Procedure

Reaction of 4,5-diphenyl-1H-imidazole (300 mg, 1.36 mmol), NaH (60%, 55 mg, 1.36 mmol), and SEMCl (289 uL, 1.63 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (304 mg, 64%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.88 (t, 2H, J=7.5 Hz), 3.46 (t, 2H, J=9.0 Hz), 5.12 (s, 2H), 7.27–7.38 (m, 3H), 7.40–1.52 (m, 7H), 7.75 (s, 1H).

Source