Water → Ethyl 4-oxo-2-propylpentanoate

HRID 1627782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1627782
[CH3:1][C:2]1([CH2:7][CH:8]([CH2:14][CH2:15][CH3:16])[C:9]([O:11][CH2:12][CH3:13])=[O:10])OCC[O:3]1.O.C(OCC)(=O)C>CCCCCC.ClCCl>[O:3]=[C:2]([CH3:1])[CH2:7][CH:8]([CH2:14][CH2:15][CH3:16])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Komponenten

6

Edukt 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 58725309Ethyl 2-((2-methyl-1,3-dioxolan-2-yl)methyl)pentanoate

Produkt 1

HCID 58725287Ethyl 4-oxo-2-propylpentanoateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

To a solution of ethyl 2-((2-methyl-1,3-dioxolan-2-yl)methyl)pentanoate (9.8 g; 42.55 mmol) in hexane (106 mL) at −78° C. under nitrogen atmosphere was added borontribromide (55 mL; 55 mmol; 1M in dichloromethane) and the reaction mixture was stirred at −20° C. for 2 h. Water (50 mL) and ethyl acetate (50 mL) were added to the reaction mixture and the layers were separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulphatesulphate, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (1-40%) in heptane furnished 6.41 g (81%) of ethyl 4-oxo-2-propylpentanoate as a light yellow oil.

Aufarbeitung

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulphatesulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (1-40%) in heptane

Quellen und Nachweise

ORD-Eintrag
ord-55e18f13baad4cbf9d403f78e7b9d1a4
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785638B2

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