Sodium Sulfate → 1-(4-Fluorophenyl)propan-1-ol

HRID 2086208

Reaktionsgleichung

Reaktionsgleichung von HRID 2086208
C(O[C:4](=O)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=[O:22].[Na+].[Na+]>C(OCC)(=O)C.O1CCCC1.[Rh]>[F:13][C:10]1[CH:11]=[CH:12][C:7]([CH:6]([OH:22])[CH2:5][CH3:4])=[CH:8][CH:9]=1

Komponenten

7

Edukt 3

HCID 24436Sodium SulfateHCID 367200Ethyl 3-(4-fluorophenyl)prop-2-enoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 1024701-(4-Fluorophenyl)propan-1-olAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23948RhodiumKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

This ester (6.52 g, 33.6 mmol) was dissolved in ethyl acetate (100 ml), and 5% rhodium/alumina (1.30 g) was added thereto followed by stirring under a hydrogen atmosphere for 8 hours at room temperature. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure, and then the residue was dissolved in anhydrous tetrahydrofuran (30 ml). This solution was added dropwise to a suspension of lithium aluminium hydride (126 g, 33.2 mmol) in anhydrous tetrahydrofuran (60 ml) in the ice bath. The reaction mixture was stirred for 30 minutes at the same temperature, and a saturated aqueous sodium sulfate solution was added thereto followed by stirring for 10 minutes at room temperature. The mixture was filtered through Celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=5:1-1:1) to give 4-fluorophenylpropan-1-ol (4.86 g, 95% yield) as a colorless oil.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in anhydrous tetrahydrofuran (30 ml)
  4. stirringThe reaction mixture was stirred for 30 minutes at the same temperature
  5. stirringby stirring for 10 minutes at room temperature
  6. filtrationThe mixture was filtered through Celite
  7. extractionthe filtrate was extracted with ethyl acetate
  8. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated in vacuo
  11. customthe residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=5:1-1:1)

Quellen und Nachweise

ORD-Eintrag
ord-269a57a0e48a4bd78b4200c4bca9df60
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06723745B2

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