Imidazole → 2-[2-(t-Butyldiphenylsilyloxy)ethylthio]ethanol

HRID 748792

Reaktionsgleichung

Reaktionsgleichung von HRID 748792
[S:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].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)(=O)C>ClCCl>[Si:17]([O:4][CH2:3][CH2:2][S:1][CH2:5][CH2:6][OH:7])([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 5447ThiodiglycolHCID 8857Ethyl AcetateHCID 94078tert-Butyldiphenylchlorosilane

Produkt 1

HCID 597508072-[2-(t-Butyldiphenylsilyloxy)ethylthio]ethanolAusbeute 54,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In dichloromethane (200 ml) were dissolved 2,2′-thiodiethanol (10.0 g, 81.8 mmol) and imidazole (4.70 g, 69.0 mmol), followed by the dropwise addition of t-butylchlorodiphenylsilane (15.0 ml, 57.7 mmol) at room temperature. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 14 hours. After concentration under reduced pressure, diethyl ether was added to the residue. Then, the insoluble matter was filtered off. The residue obtained by concentrating the filtrate under reduced pressure was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated under reduced pressure, whereby the title compound (11.3 g, 31.3 mmol, 54%) was obtained as a colorless oil.

Aufarbeitung

  1. additionAfter completion of the dropwise addition
  2. concentrationAfter concentration under reduced pressure, diethyl ether
  3. additionwas added to the residue
  4. filtrationThen, the insoluble matter was filtered off
  5. customThe residue obtained
  6. concentrationby concentrating the filtrate under reduced pressure
  7. customthe fraction obtained from the hexane

Quellen und Nachweise

ORD-Eintrag
ord-b676ef213e204279a50daff62ebef92f
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399775B2

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