Imidazole → 4-bromo-3-(1-((tert-butyldimethylsilyl)oxy)ethyl)-1H-isochromen-1-one

Participants

Reaction Steps

4-Bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one (intermediate A2, 5 g, 18.658 mmol) was dissolved in DCM (50 ml); imidazole (2.54 g, 37.3 mmol) and tert-butyl(chloro)dimethylsilane (5.624 g, 37.3 mmol) were added and the mixture was stirred at RT for 1 hr. The mixture was washed with brine, the organic phase was dried over sodium sulfate and solvent removed under reduced pressure to afford a crude which was purified by flash chromatography on silica gel Biotage column (cyclohexane:EtOAc=95:5 to 60:40) affording title compound as a white solid (6.5 g, 16.97 mmol, 91%).

Provenance & Evidence