Réaction #502111

ord-7ab72a1b4004402e9802876b8ec4acd9

Équation de réaction

CC1(C)OC[C@@H](CO)O1
((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methan-1-ol
CCN(CC)CC
triethylamine
CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1
tert-butylchlorodiphenylsilane
CC1(C)OC[C@@H](CO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)O1
title compound
Rendement 106.2%
CC1(C)OC[C@@H](CO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)O1
1-(((4S)-2,2-Dimethyl(1,3-dioxolan-4-yl))methoxy)-2,2-dimethyl-1,1-diphenyl-1-silapropane
Rendement 106.2%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Lavagethe reaction mixture was washed with water, brine
  2. 2
    Séchagedried over sodium sulfate
  3. 3
    Filtrationfiltered
  4. 4
    Autreevaporated

Mode opératoire

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

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08088762B2uspto-grants-2012_01