Hydrochloric Acid → 4-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenol

HRID 1095200

Reaktionsgleichung

Reaktionsgleichung von HRID 1095200
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].Br[CH2:10][CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C.O>[C:16]([Si:13]([CH3:15])([CH3:14])[O:12][CH2:11][CH2:10][O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)([CH3:19])([CH3:18])[CH3:17]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 10796Cesium carbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Produkt 1

HCID 220333784-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of hydroquinone (Aldrich, 11.01 g, 100 mmol) in DMF (300 mL), (2-bromo-ethoxy)-tert-butyl-dimethyl-silane (Aldrich, 12.0 g, 50 mmol), cesium carbonate (40.7 g, 125 mol) were added and the mixture was stirred at 60° C. overnight. The mixture was poured into water (300 mL) and 6N HCl was added to adjust the “pH” to 6. The mixture was extracted with EtOAc (3×60 mL) and the extracts were combined and dried. Removal of solvent gave the crude, which was chromatographied on a ISCO machine eluting with EtOAc/hexane (0-30%) to give a light brown solid. 5.71 g.

Aufarbeitung

  1. additionwas added
  2. extractionThe mixture was extracted with EtOAc (3×60 mL)
  3. customdried
  4. customRemoval of solvent
  5. customgave the crude, which
  6. washeluting with EtOAc/hexane (0-30%)
  7. customto give a light brown solid

Quellen und Nachweise

ORD-Eintrag
ord-2448f86660f7407980735a152a45a52e
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134001B2

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