Water → HCID 14410054, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(tert-butyldimethylsilanyloxymethyl)-1H-imidazole (Amino, Y.; Eto, H.; Eguchi, C., Chem. Pharm. Bull., 1989, 37, 1481-1487) (3.158 g, 14.9 mmol) in anhydrous THF (25 ml), cooled to −78° C. under nitrogen, was added a 1.6 M solution of butyllithium in hexanes (10.2 ml, 16.4 mmol). The mixture was stirred under nitrogen at −78° C. for 30 min, then iodomethane (0.97 ml, 15.6 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 5 h. Water (150 ml) was then added and the mixture was extracted with diethyl ether (150 ml). The organic extract was washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography (alumina, 40% EtOAc/hexane) to yield 0.4732 g (14%) of 4-(tert-butyldimethylsilanyloxymethyl)-1-methyl-1H-imidazole and 1.463 g (43%) of 5-(tert-butyldimethylsilanyloxymethyl)-1-methyl-1H-imidazole.

Provenance & Evidence