Reaction #7210

Reaction equation

5-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1H-imidazole

NaH

SEMCl

→

title compound

Yield 52.0%

5-(5,6,7,8-Tetrahydro-naphthalen-2-yl)-1-(2-trimethylsilanyl ethoxymethyl)-1H-imidazole

Yield 52.0%

Conditions

Procedure

Reaction of 5-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1H-imidazole (387 mg, 1.95 mmol), NaH (60%, 76 mg, 1.89 mmol), and SEMCl (474 uL, 2.28 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (321 mg, 52%) as a brown oil. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.92 (t, 2H, J=9.0 Hz), 1.80–1.83 (m, 4H), 2.77–2.81 (m, 4H), 3.51 (t, 2H, J=9.0 Hz), 5.28 (s, 2H), 7.08 (d, 1H, J=9.0 Hz), 7.29 (s, 1H), 7.48 (d, 1H, J=6.0 Hz), 7.54 (s, 1H), 7.61 (s, 1H).

Source