Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate → Ethyl 1-methyl-4-oxocyclohexanecarboxylate

HRID 1913268

Reaktionsgleichung

Reaktionsgleichung von HRID 1913268
[CH3:1][C:2]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:11][CH2:10][C:5]2(OCC[O:6]2)[CH2:4][CH2:3]1.[N+]([O-])([O-])=O.[Ce].[NH4+]>C(#N)C.O>[CH3:1][C:2]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:3][CH2:4][C:5](=[O:6])[CH2:10][CH2:11]1

Komponenten

5

Edukt 2

HCID 19004805Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylateHCID 57418452Ammonium cerium-nitrate

Produkt 1

HCID 21911973Ethyl 1-methyl-4-oxocyclohexanecarboxylateAusbeute 101,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel3×HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate (Int-18b, 2.09 g, 9.17 mmol) was dissolved in acetonitrile (100 mL) and water (50 mL). Ammonium cerium nitrate (503 mg, 0.92 mmol) in water (50 mL) was added and the resulting mixture was heated up to 70° C. and stirred for 1 h. After being cooled down to room temperature, water (100 mL) was added and the mixture was extracted with ether (100 mL×3). The combined organics were washed with water, brine and dried. After concentration, the residue was purified on a column (silica gel, 0-30% ethyl acetate in hexane) which gave ethyl 1-methyl-4-oxocyclohexanecarboxylate (Int-18c) (1.72 g) as an oil.

Aufarbeitung

  1. temperatureAfter being cooled down to room temperature
  2. extractionthe mixture was extracted with ether (100 mL×3)
  3. washThe combined organics were washed with water, brine
  4. customdried
  5. concentrationAfter concentration
  6. customthe residue was purified on a column (silica gel, 0-30% ethyl acetate in hexane) which

Quellen und Nachweise

ORD-Eintrag
ord-05e4d28d91c34094b81f567dce02b417
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609675B2

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