Imidazole → HCID 57346940, compound

Participants

Reaction Steps

To a stirred solution of tert-butyldimethylsilyl chloride (16.6 g, 0.11 mol) and imidazole (16.3 g, 0.24 mol) in DMF (20 mL) was added 4-pyridinemethanol (10 g, 0.09 mol) and the mixture was stirred for about 1 h. The reaction mixture was poured into diethyl ether (200 mL) and the resulting solution was washed with water (100 mL). The aqueous phase was extracted with diethyl ether and the combined organic phases are washed with water, brine and dried (MgSO4). The solvent was evaporated under reduced pressure to leave 4-(tertbutyidimethylsilyloxymethyl)pyridine, 22.5 g. 1H NMR (d6-DMSO) d 8.49 (d, 2H), 7.27 (d, 2H), 4.62 (s, 2H), 0.9 (s, 9H), 0.09 (s, 6H).

Provenance & Evidence