Ethyl Acetate → Ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

HRID 7677

Reaktionsgleichung

Reaktionsgleichung von HRID 7677
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C([C:24]([O:26][CH2:27][CH3:28])=[O:25])#N.CCOC(C)=O>C1COCC1.O>[CH2:27]([O:26][C:24]([CH:8]1[C:7](=[O:10])[CH2:6][CH2:5][C:4]2([O:3][CH2:2][CH2:1][O:11]2)[CH2:9]1)=[O:25])[CH3:28]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 69336Ethyl cyanoformateHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 559688Ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

1,4-Cyclohexanedione mono-ethylene ketal (25 g) was dissolved in THF and cooled to −78° C. 1.0 M Lithium bis(trimethylsily)amide (160 mL) in THF was added dropwise. After 30 min, ethyl cyanoformate (15.9 mL) was added dropwise. After 60 min, the solution was poured into EtOAc and water containing ice. The organic layer was washed with water and brine before it was dried and concentrated. This crude was filtered through a plug of silica to give the 8-oxo-1,4-dioxa-spiro[4.5]decane-7-carboxylic acid ethyl ester (32.4 g). MS found: (M+H)+=228.9.

Aufarbeitung

  1. waitAfter 60 min
  2. additioncontaining ice
  3. washThe organic layer was washed with water and brine before it
  4. customwas dried
  5. concentrationconcentrated
  6. filtrationThis crude was filtered through a plug of silica

Quellen und Nachweise

ORD-Eintrag
ord-93b60822344942a1918edaf6b1b87f2d
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087604B2

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