Imidazole → 3-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridine

Participants

Reaction Steps

To a solution of 2-chloro-3-(hydroxymethyl)pyridine (Read, M. W; and Ray, P. S.; J. Heterocyclic. Chem., 1995, 32, 1595-1597., 2.81 g, 19.1 mmol) and imidazole (3.25 g, 47.7 mmol) in N,N-dimethylformamide (30 ml) was added tert-butyldimethylsilyl chloride (3.74 g, 24.8 mmol) at 0° C. The mixture was allowed to warm to room temperature and stirred for 17 h. The solution was diluted with diethyl ether (200 ml), and the resulting solution was washed with water (100 ml×3), and dried (MgSO4). Removal of solvent gave an oily residue. Purification by flash column chromatography eluting with ethyl acetate/hexane (1:15) afforded 3.61 g (73%) of the title compound.

Provenance & Evidence