Imidazole → Tert-butyl((2-iodoallyl)oxy)dimethylsilane

Participants

Reaction Steps

A stirred solution of 2-iodoprop-2-en-1-ol (24 g, 130.4 mmol) in dry dichloromethane (500 mL) was cooled to 0° C. Imidazole (17.75 g, 260.9 mmol) was added in several portions, and the mixture was stirred for 10 minutes. Tert-butyldimethylsilyl chloride (29.49 g, 195.9 mmol) was added in several portions at 0° C., and the reaction mixture was slowly warmed to room temperature and stirred for 3 h. The reaction mixture was quenched with water (100 mL), and the organic phase was separated. The organic phase was washed with brine (100 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure (water bath temperature <25° C.). The residue was purified by column chromatography using 100% petroleum ether as eluent to afford tert-butyl((2-iodoallyl)oxy)dimethylsilane.

Provenance & Evidence