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

HRID 23783
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 23783
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

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 21908982
Water methylene chloride
Lösungsmittel

Versuchsvorschrift

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

Quellen und Nachweise

ORD-Eintrag
ord-1c47ced5a42f41fc94e54e9b138b5b44
Quelldatensatz
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06852880B2

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