2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → (S)-3-(t-butyldimethylsilyloxy)-5-phenyl-pentan-1-ol

HRID 1611742

Reaktionsgleichung

Reaktionsgleichung von HRID 1611742
[Si:1]([O:8][C@H:9]([CH2:18][CH2:19][O:20]CC1C=CC(OC)=CC=1)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.C([O-])(O)=O.[Na+]>ClCCl.O>[Si:1]([O:8][C@@H:9]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:18][CH2:19][OH:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 516892Sodium BicarbonateHCID 69589755(S)-3-(t-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-1-phenyl pentane

Produkt 1

HCID 69589993(S)-3-(t-butyldimethylsilyloxy)-5-phenyl-pentan-1-olAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21908982Water methylene chlorideLösungsmittel

Versuchsvorschrift

(S)-3-(t-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-1-phenyl pentane (15 g, 36.2 mmol) was dissolved in a solvent mixture of dichloromethane-water (20:1) (252 ml) DDQ (8.2 g, 36.2 mmol) was added thereto and the mixture was stirred for 30 minutes at room temperature. After completion of the reaction, saturated aqueous NaHCO3 solution (100 ml) was added to the reaction solution to stop the reaction. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to give (S)-3-(t-butyldimethylsilyloxy)-5-phenyl-pentan-1-ol (10.6 g, Yield 99%) of a yellow oil.

Aufarbeitung

  1. additionwas added
  2. additionwas added to the reaction solution
  3. customthe reaction
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with dichloromethane
  6. washwashed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1)

Quellen und Nachweise

ORD-Eintrag
ord-76fadddb889c48e281915b234f36a60a
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06989458B2

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