Imidazole → Tert-butyldimethyl(2-(thiophen-2-YL)ethoxy)silane

Participants

Reaction Steps

Tert-butyldimethylsilyl chloride (15.5 g, 103 mmol) was added portionwise to a solution of 2-(2-thienyl)ethanol (11.0 g, 85.9 mmol) and imidazole (7.0 g, 103 mmol) in N,N-dimethylformamide (35 mL). The resultant solution was stirred at room temperature for 18 h. The reaction mixture was partitioned between ethyl acetate (30 mL) and water (30 mL) and the organic phases washed with water (3×50 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with 1-4% ethyl acetate in iso-hexane to give the title compound as a colourless oil (20 g, 96%).

Provenance & Evidence