Hydrochloric Acid → 2,2,2-Trifluoro-1-(4-furan-3-yl-phenyl)-ethanol

HRID 1620824

Reaktionsgleichung

Reaktionsgleichung von HRID 1620824
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:19]1[CH:23]=[CH:22][C:21]([C:24]2[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=2)=[CH:20]1.[F:32][C:33]([Si](C)(C)C)([F:35])[F:34].Cl>C1COCC1>[F:32][C:33]([F:35])([F:34])[CH:28]([C:27]1[CH:30]=[CH:31][C:24]([C:21]2[CH:22]=[CH:23][O:19][CH:20]=2)=[CH:25][CH:26]=1)[OH:29]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 215260454-(Furan-3-Yl)Benzaldehyde

Produkt 1

HCID 667436042,2,2-Trifluoro-1-(4-furan-3-yl-phenyl)-ethanolAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Tetrabutylammonium fluoride (0.024 ml; 1.0 M solution in tetrahydrofuran) was added to a solution of 4-furan-3-yl-benzaldehyde (410 mg, 2.38 mmol) and trifluoromethyltrimethylsilane (TMSCF3) (423 μl, 2.86 mmol) in 5 ml THF at 0° C. The formed mixture was warmed up to room temperature and stirred at room temperature for 4 hours. The reaction mixture was then treated with 5 ml of 1N HCl and stirred at room temperature overnight. The product was extracted with ethyl acetate (3×50 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 480 mg of 2,2,2-trifluoro-1-(4-furan-3-yl-phenyl)-ethanol, yield: 83%.

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. extractionThe product was extracted with ethyl acetate (3×50 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customThe organic solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-605860cd0bd1486780a6bf7d807dad77
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772482B2

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