4-Toluenesulfonyl chloride → 2-(2,2,2-Trifluoroethoxy)ethyl p-toluenesulfonate

HRID 658259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658259
[F:1][C:2]([F:9])([F:8])[CH2:3][O:4][CH2:5][CH2:6][OH:7].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:20][C:10]1[CH:15]=[CH:14][C:13]([S:16]([O:7][CH2:6][CH2:5][O:4][CH2:3][C:2]([F:9])([F:8])[F:1])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 2558542-(2,2,2-Trifluoroethoxy)ethan-1-ol

Produkt 1

HCID 220332952-(2,2,2-Trifluoroethoxy)ethyl p-toluenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(2,2,2-trifluoroethoxy)ethanol (1 eq.) in DCM (0.2 M) was added p-toluenesulfonyl chloride (1.3 eq.) and triethylamine (1.5 eq.). The reaction was stirred at rt for 18 h. The reaction was quenched with saturated NH4Cl aqueous solution and extracted with DCM. The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 30% ether in hexane) to afford the title compound as an oil.

Aufarbeitung

  1. customThe reaction was quenched with saturated NH4Cl aqueous solution
  2. extractionextracted with DCM
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography (SiO2, 30% ether in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4b06a8c6e19b40db9fb6084cc28ddb2e
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076359B2

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