Imidazole → Ethanone, 1-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-

Participants

Reaction Steps

N,N-dimethylformamide (70 ml), was mixed with 5.00 g (36.7 mmol), of 4′-hydroxyacetophenone, 6.64 g (44.1 mmol), of tert-butyldimethylchlorosilane, and 6.00 g (88.1 mmol), of imidazole and the mixture was stirred for 12 hours at room temperature. The reaction mixture was poured onto ice water to stop the reaction and extracted with 100 ml of ethyl acetate. The organic extract was washed with 100 ml of water ten times and then with saturated saline and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform 100%), to obtain 5.23 g (yield: 56.9%), of the target compound.

Provenance & Evidence