Sodium hydride → 2-[(Tert-butyldimethylsilyloxy)methyl]benzylalcohol

HRID 1978327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1978327
[C:1]1([CH2:9][OH:10])[C:2]([CH2:7][OH:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[H-].[Na+].[C:13]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])([CH3:15])[CH3:14]>COCCOC.O>[Si:17]([O:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH2:9][OH:10])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:19])[CH3:18]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 691531,2-Benzenedimethanol

Produkt 1

HCID 108484452-[(Tert-butyldimethylsilyloxy)methyl]benzylalcohol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 14.074 g (101.86 mM) of 1,2-benzenedimethanol in 100 ml of 1,2-dimethoxyethane was added 4.07 g (102 mM) of a liquid paraffin suspension of 60% sodium hydride at room temperature and the mixture was stirred at the prevailing temperature for one hour. To this reaction mixture was added a solution of 15.4 g (102 mM) of tert-butylchlorodimethylsilane in 50 ml of 1,2-dimethoxyethane dropwise, and the mixture was stirred at room temperature overnight. This reaction mixture was poured in water and extracted with 3 portions of ethyl acetate. The organic layers were combined and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 3/1) to provide the title compound.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionextracted with 3 portions of ethyl acetate
  3. dry with materialdried over MgSO4
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 3/1)

Quellen und Nachweise

ORD-Eintrag
ord-036afe05e6574a948a0338c076fbe3cc
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235731B1

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