Imidazole → 2-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethyl tert-butyl(diphenyl)silyl ether

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Reaction Steps

To a solution of 2-((1S)-6-bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol (3.0 g, 11.7 mmol) in dry THF (100 mL) was added imidazole (3.97 g, 58.4 mmol) and chloro-tert-butyl(diphenyl)silane (6.42 g, 23.4 mmol), and the mixture stirred under nitrogen at room temperature for 20 h. Diethyl ether was added and the mixture filtered through a pad of silica. The filtrate was evaporated in vacuo and the crude product purified by flash chromatography on silica, eluting with ethyl acetate/heptane (0:10 to 2:8), to yield the title compound.

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