Imidazole → HCID 178455371, Verbindung

HRID 1095146

Reaktionsgleichung

Reaktionsgleichung von HRID 1095146
[C@H:1]1([OH:8])[CH2:6][CH2:5][C@H:4]([OH:7])[CH2:3][CH2:2]1.N1C=CN=C1.[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15]>CN(C)C=O>[C:14]([Si:18]([CH3:21])([CH3:20])[O:7][C@H:4]1[CH2:5][CH2:6][C@H:1]([OH:8])[CH2:2][CH2:3]1)([CH3:17])([CH3:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178521615HCID 178521615, Verbindung

Produkt 1

HCID 178455371HCID 178455371, VerbindungAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of trans-1,4-cyclohexanediol (3 g, 26 mmol) in anhydrous N,N-dimethylformamide (30 mL) at 0° C. was added imidazole (1.7 g, 26 mmol) and tert-butyldimethylchlorosilane (3.87 g, 26 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;2) to give trans-4-(tert-buyl-dimethyl-silanyloxy)-cyclohexanol as a white solid (3.9 g, 65%).

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;2)

Quellen und Nachweise

ORD-Eintrag
ord-2ee3af40792347619c7d449624ac0469
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134001B2

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