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

HRID 1095107

Reaktionsgleichung

Reaktionsgleichung von HRID 1095107
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.N1C=CN=C1.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O>[C:17]([Si:21]([CH3:24])([CH3:23])[O:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:20])([CH3:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 98340144-(2-Hydroxyethoxy)phenol

Produkt 1

HCID 220333784-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenolAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-(2-hydroxy-ethoxy)-phenol (4.2 g, 27 mmol) in anhydrous N,N-dimethylformamide (30 mL) at 0° C. was added imidazole (2.1 g, 31 mmol) and tert-butyldimethylchlorosilane (4 g, 27 mmol). The reaction mixture was then stirred at 0° C. for 1 h. The mixture was partitioned between ethyl acetate and water. Organic layer was separated, aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1;4) to give 4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenol as a colorless oil (5.1 g, 70%)

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customOrganic layer was separated
  3. extractionaqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (EtOAc:hexanes=1;4)

Quellen und Nachweise

ORD-Eintrag
ord-ce0f28087fc84ddba86a8b087ffac0a1
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134001B2

Verknüpfte Notizen

Wird geladen…