2-Cyclohexylethanol → HCID 86658987, Verbindung

HRID 475522

Reaktionsgleichung

Reaktionsgleichung von HRID 475522
[H-].[Na+].[CH:3]1([CH2:9][CH2:10][OH:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[C:15]([C:21]([F:24])([F:23])[F:22])[CH:14]=1>CN(C)C=O>[CH:3]1([CH2:9][CH2:10][O:11][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[C:15]([C:21]([F:22])([F:24])[F:23])[CH:14]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Komponenten

5

Edukt 3

HCID 205082-CyclohexylethanolHCID 24758Sodium hydrideHCID 5229404-Fluoro-2-(trifluoromethyl)benzaldehyde

Produkt 1

HCID 86658987HCID 86658987, VerbindungAusbeute 75,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Sodium hydride (343.2 mg, 8.58 mmol, 60% dispersed oil) was slowly added to cyclohexaneethanol (1 g, 7.8 mmol) dissolved in 30 ml of dried dimethylformamide under nitrogen at room temperature while stirring. The mixture was further stirred at room temperature for 30 minutes. Then, 4-fluoro-2-(trifluoromethyl)benzaldehyde (1.2 g, 7.8 mmol) dissolved in dried dimethylformamide was added thereto over 10 minutes and stirred at room temperature for 18 hours until the initial product disappeared. Subsequently, ice water was added thereto, and the resulting mixture was extracted with ethyl acetate and water. The organic layer was washed with water several times, dried with anhydrous magnesium sulfate, filtered and solvent-evaporated. The residual oil was chromatographed on the silica gel column (hexane:ethyl acetate-20:1) to afford the intermediate, 4-(2-cyclohexylethoxy)-2-(trifluoromethyl)benzaldehyde (1.77 g, yield: 75.6%).

Aufarbeitung

  1. stirringThe mixture was further stirred at room temperature for 30 minutes
  2. additionwas added
  3. extractionthe resulting mixture was extracted with ethyl acetate and water
  4. washThe organic layer was washed with water several times
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customsolvent-evaporated
  8. customThe residual oil was chromatographed on the silica gel column (hexane:ethyl acetate-20:1)

Quellen und Nachweise

ORD-Eintrag
ord-9c081e498bc144e4aa60dc4f5d0a06c4
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637558B2

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