Imidazole → cis-4-((t-Butyldimethylsilyl)oxy)cyclohexan-1-ol

HRID 1025679

Reaktionsgleichung

Reaktionsgleichung von HRID 1025679
[CH:1]1([OH:8])[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.N1C=CN=C1.CCN(CC)CC.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(Cl)Cl.O>[Si:21]([O:7][CH:4]1[CH2:5][CH2:6][CH:1]([OH:8])[CH2:2][CH2:3]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 111621,4-CyclohexanediolHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

HCID 554539cis-4-((t-Butyldimethylsilyl)oxy)cyclohexan-1-olAusbeute 42,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1,4-cyclohexanediol (5 g, 43 mmol), imidazole (2.92 g, 43 mmol) and NEt3 (7 mL) in CH2Cl2 (100 mL) cooled in an ice bath was added tert-butyldimethylsilyl chloride (6.47 g, 43 mmol). The mixture was stirred at room temperature overnight. Water was added and the organic phase was separated. The aqueous layer was extracted with EtOAc. The combined organic phase was dried over MgSO4 and concentrated. Chromatography on silica gel eluting with 3:1 EtOAc/hexanes provided the title compound (4.2 g, 42%) as an oil. MS calculated (M+H)+ 231, found 231.

Aufarbeitung

  1. customthe organic phase was separated
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-641883d1c79e41cca71d57f46bfb14ed
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729063B2

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