Imidazole → 2-(Tert-butyldimethylsilanyloxy)-1-phenylethanone

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Reaction Steps

To a solution of 2-hydroxyacetophenone (10 g, 74.5 mmol) and imidazole (15 g, 220 mmol) in N,N-dimethylformamide (50 ml) was added tert-butyldimethylchlorosilane (22 g, 146 mmol) at room temperature for 6 hours. The mixture was poured into water (200 ml) and extracted twice with 200 ml of ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=1/1) to give 2-(tert-butyldimethylsilanyloxy)-1-phenylethanone (8.0 g, 31.9 mmol, 43%) as a yellow oil.

Provenance & Evidence