Hydroquinone → 4-(tert-Butyldimethylsiloxy)phenol

Participants

Reaction Steps

To an ice-cooled solution of hydroquinone (Compound 17; 3.3 g, 30 mmol) in DMF (60 ml), a solution of imidazole (3.1 g, 45 mmol) and tert-butyldimethylsilyl chloride (4.5 g, 30 mmol) in DMF (30 ml) was added; the ice bath was removed, and this was followed by overnight stirring at room temperature. This was poured over water to stop the reaction, after which extraction from ether was conducted. The combined organic phases were washed with saturated brine, thereafter dried with sodium sulfate. After filtration and concentration under reduced pressure, the residue obtained was purified by silica gel column chromatography [Biotage, eluent (9:1 n-hexane:ethyl acetate)] to yield Compound 18 (white solid 3.6 g, 53%).

Provenance & Evidence