Potassium Carbonate → (R)-1-(tert-butyldimethylsilyloxy)pent-4-yn-2-ol

HRID 1895529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1895529
C(=O)([O-])[O-].[K+].[K+].[Si:7]([O:14][CH2:15][C@H:16]([OH:24])[CH2:17][C:18]#[C:19][Si](C)(C)C)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>CO>[Si:7]([O:14][CH2:15][C@H:16]([OH:24])[CH2:17][C:18]#[CH:19])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 53308767(R)-1-((tert-Butyldimethylsilyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol

Produkt 1

HCID 86667884(R)-1-(tert-butyldimethylsilyloxy)pent-4-yn-2-olAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Potassium carbonate (2.14 g, 15.5 mmol) was added to a solution of (R)-1-(tert-butyldimethylsilyloxy)-5-(trimethylsilyl)pent-4-yn-2-ol (3 g, 10.6 mmol) in methanol (100 mL) and the mixture stirred at room temperature for 8 hours. The solvent was removed under reduced pressure and aqueous ammonium chloride solution (100 mL) was added to the resulting oil. The mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The crude material was purified by flash chromatography (biotage) using a gradient of EtOAc in hexane to afford (R)-1-(tert-butyldimethylsilyloxy)pent-4-yn-2-ol (1.81 g, 8.44 mmol, 80%).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure and aqueous ammonium chloride solution (100 mL)
  2. additionwas added to the resulting oil
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash chromatography (biotage)

Quellen und Nachweise

ORD-Eintrag
ord-56195a7f67f04d11aeea6851bc14b164
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513443B2

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