Imidazole → 4-(t-Butyldiphenylsilyloxy)-1-methyl-1-butanol

HRID 748693

Reaktionsgleichung

Reaktionsgleichung von HRID 748693
[CH2:1]([OH:7])[CH2:2][CH2:3][CH:4]([OH:6])[CH3:5].N1C=CN=C1.[C:13]([Si:17](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:16])([CH3:15])[CH3:14].C(OCC)C>CN(C)C=O>[Si:17]([O:7][CH2:1][CH2:2][CH2:3][CH:4]([CH3:5])[OH:6])([C:13]([CH3:16])([CH3:15])[CH3:14])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 79083Pentane-1,4-diolHCID 94078tert-Butyldiphenylchlorosilane

Produkt 1

HCID 230285714-(t-Butyldiphenylsilyloxy)-1-methyl-1-butanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In N,N-dimethylformamide (200 ml) were dissolved 1,4-pentanediol (10.0 g, 96.0 mmol) and imidazole (6.6 g, 96.9 mmol). Under ice cooling, t-butyl chlorodiphenylsilane (25.2 ml, 96.4 mmol) was added dropwise. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 2 days. To the reaction mixture was added diethyl ether, followed by washing with water. The organic layer was dried over anhydrous magnesium sulfate. After filtration, the residue obtained by concentrating the filtrate under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=5:1), whereby the title compound (32.0 g, 97%) was obtained as a colorless oil.

Aufarbeitung

  1. additionAfter completion of the dropwise addition
  2. washby washing with water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe residue obtained
  6. concentrationby concentrating the filtrate under reduced pressure
  7. customwas purified by silica gel chromatography (hexane:ethyl acetate=5:1), whereby the title compound (32.0 g, 97%)
  8. customwas obtained as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-70b62e78ab69429c94b4d30757a4585a
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399775B2

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