Reaction #502111

Reaction equation

((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methan-1-ol

triethylamine

tert-butylchlorodiphenylsilane

→

title compound

Yield 106.2%

1-(((4S)-2,2-Dimethyl(1,3-dioxolan-4-yl))methoxy)-2,2-dimethyl-1,1-diphenyl-1-silapropane

Yield 106.2%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Washthe reaction mixture was washed with water, brine
2. 2
   Dryingdried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Otherevaporated

Procedure

To a solution of ((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methan-1-ol (9 g, 68.6 mmol) in anhydrous dichloromethane (40 mL) were added triethylamine (11.2 mL), tert-butylchlorodiphenylsilane (19.8 g, 372 mmol), and N,N-dimethylaminopyridine (DMAP, 418 mg, 3.4 mmol) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred at room temperature overnight. It was then diluted with additional dichloromethane and the reaction mixture was washed with water, brine, dried over sodium sulfate, filtered and evaporated to give the title compound (27 g) which was used in the next step without further purification.

Source