Imidazole → 2-[(tert-Butyldimethylsilyl)oxymethyl]-6-chlorobenzyl alcohol

Participants

Reaction Steps

A solution of 3-chloro-1,2-benzenedimethanol (described in J. Chem. Soc., p. 5050 (1952); 3.02 g, 17.5 mmol) in tetrahydrofuran (40 ml) was cooled to 0° C., and then imidazole (1.19 g, 17.5 mmol) and tert-butylchlorodimethylsilane (2.64 g, 17.5 mmol) were added thereto. The mixture was stirred at room temperature for 1 hour, then water was added thereto, and the product was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure to give a residue. The residue was subjected to chromatography on a silica gel (100 g) column (eluent; ethyl acetate:hexane=1:5) to afford the title compound (3.69 g, 73% yield) as a colorless oil.

Provenance & Evidence