Water → (S)-3-(t-butyldiphenylsilyloxy)-2-methylpropanal

HRID 1609786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1609786
[Si:1]([O:18][CH2:19][C@H:20]([CH3:23])[CH2:21][OH:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1.O>ClCCl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[Si:1]([O:18][CH2:19][C@H:20]([CH3:23])[CH:21]=[O:22])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 117718171-Propanol, 3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-methyl-, (R)-

Produkt 1

HCID 11782372(S)-3-(t-butyldiphenylsilyloxy)-2-methylpropanalAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under argon atmosphere, (R)-3-(t-butyldiphenylsilyloxy)-2-methylpropanol (48) (725 mg, 2.2 mmol) was dissolved in 40 ml of dry dichloromethane. MS-4A (30 mg), NMO (862 mg, 11.1 mmol) and TPAP (catalytic amount) were added to the resultant solution at 0° C., and the mixture was stirred for 15 min. The reaction mixture was further stirred overnight after the temperature was returned to room temperature. Subsequently, H2O was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over magnesium sulfate and evaporated. The obtained crude product was purified by column chromatography (21 g, 4% AcOEt-hexane) to obtain a colorless oily product (49) (700 mg, 97%).

Aufarbeitung

  1. waitThe reaction mixture was further stirred overnight
  2. customwas returned to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe obtained crude product
  8. customwas purified by column chromatography (21 g, 4% AcOEt-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-90f0904651e848bf81aa9c849b408204
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06982257B1

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