Reaction #7218

Reaction equation

4-(4-fluoro-phenyl)-1H-imidazole

NaH

SEMCl

→

title compound

Yield 67.3%

4-(4-Fluorophenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole

Yield 67.3%

Conditions

Workup

1. 1
   Otherfollowed by purification of the crude material on silica gel (50% EtOAc/hexanes)

Procedure

Reaction of 4-(4-fluoro-phenyl)-1H-imidazole (573 mg, 3.53 mmol), 95% NaH (100 mg, 4.0 mmol), and SEMCl (650 mg, 3.90 mmol) followed by purification of the crude material on silica gel (50% EtOAc/hexanes) gave the title compound as yellow crystals (695 mg, 67%). 1H NMR (CDCl3) □−0.01 (s, 9H), 0.93 (m, 2H), 3.52 (m, 2H), 5.29 (s, 2H), 7.07 (m, 2H), 7.28 (s, 1H), 7.62 (s, 1H), 7.75 (m, 2H).

Source