Water → 2-(3-(2,2-Diethoxyethoxy)phenyl)ethanol

HRID 471019

Reaktionsgleichung

Reaktionsgleichung von HRID 471019
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1.Br[CH2:18][CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22].O>CN(C=O)C>[CH2:21]([O:20][CH:19]([O:23][CH2:24][CH3:25])[CH2:18][O:16][C:12]1[CH:11]=[C:10]([CH2:9][CH2:8][OH:7])[CH:15]=[CH:14][CH:13]=1)[CH3:22]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 834043-Hydroxyphenethyl alcohol

Produkt 1

HCID 579890052-(3-(2,2-Diethoxyethoxy)phenyl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Caesium carbonate (8.84 g) was added to a solution of 3-(2-hydroxyethyl)phenol (2.5 g) and 2-bromo-1,1-diethoxyethane (3.74 g) in DMF (50 mL), and the resulting mixture was stirred at 90° C. overnight, then allowed to cool. The mixture was poured into water and extracted three times with ethyl acetate. The combined extracts were washed with water and brine, then dried over anhydrous sodium sulphate and purified by flash chromatography on silica eluted with a gradient of diethyl ether in isohexane to afford the subtitled compound as a pale yellow oil. Yield 3.0 g.

Aufarbeitung

  1. temperatureto cool
  2. extractionextracted three times with ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. custompurified by flash chromatography on silica
  6. washeluted with a gradient of diethyl ether in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-5b0a4bcb40b04ba987c3e8d067d1aeaf
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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