Reaction #7207

Reaction equation

5-(3-methoxy-phenyl)-1H-imidazole

NaH

SEMCl

→

title compound

Yield 60.0%

5-(3-Methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole

Yield 60.0%

Conditions

Procedure

Reaction of 5-(3-methoxy-phenyl)-1H-imidazole (500 mg, 2.87 mmol), NaH (60%, 112 mg, 2.79 mmol), and SEMCl (598 uL, 3.35 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (505 mg, 60%) as a brown oil. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.93 (t, 2H, J=7.5 Hz), 3.52 (t, 2H, J=9.0 Hz), 3.87 (s, 3H), 5.30 (s, 2H), 6.80–6.83 (m, 1H), 7.26–7.39 (m, 3H), 7.40 (s, 1H), 7.63 (s, 1H).

Source