Sodium Bicarbonate → tert-Butyl-dimethyl-[2-(3-oxetan-3-yl-phenyl)-ethoxy]-silane

Participants

Reaction Steps

18.3 g of 3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-benzeneboronic acid, 510 mg of NiI2, 19.9 g of sodium bis(trimethylsilyl)amide, and 250 mg of trans-2-aminocyclohexanol hydrochloride were added to 14.0 ml of 2-propanol and the mixture was stirred for 10 minutes at room temperature. Then, a solution of 10.0 g of 3-Iodo-oxetane in 6.0 ml of 2-propanol was added and the reaction mixture kept at 80° C. under microwave irradiation for 30 minutes. The reaction mixture was then poured into 100 ml of a saturated aqueous NaHCO3-solution and extracted three times using 100 ml of EA each. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP (gradient) yielded 22.0 g of the title compound, colorless oil.

Provenance & Evidence