1-Cyanovinyl acetate → Bicyclo(2.2.2)octane-2,5-dione

HRID 220229

Reaktionsgleichung

Reaktionsgleichung von HRID 220229
C[Si](C)(C)[O:3][C:4]1[CH:9]=C[CH2:7][CH2:6][CH:5]=1.C([O:15][C:16](=[CH2:19])[C:17]#N)(=O)C.C[O-].[Na+]>CO>[CH:17]12[CH2:7][CH2:6][CH:5]([C:4](=[O:3])[CH2:9]1)[CH2:15][C:16]2=[O:19]

Komponenten

5

Edukt 3

HCID 182911-Cyanovinyl acetateHCID 40956562-(Trimethylsiloxy)-1,3-cyclohexadieneHCID 10942334Sodium Methoxide

Produkt 1

HCID 13570060Bicyclo(2.2.2)octane-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

25 mL of 2-(trimethylsilyloxy)-1,3-cyclohexadiene and 13 mL of α-acetoxyacrylonitrile were mixed and heated at 150° C. in a closed vessel for 22 h. The obtained dark orange viscous oil was dissolved in 200 mL of MeOH. After dropwise addition of a solution of 2.2 g of sodium methoxide in 150 mL of MeOH the reaction mixture was stirred for 3 h at rt, poured into ice/water and extracted with DCM. The organic phases were concentrated in vacuo and the crude residue was purified by CC with EtOAc-Hept (1:2) to yield 7.9 g of rac-(1R*,4R*)-bicyclo[2.2.2]octane-2,5-dione.

Aufarbeitung

  1. extractionextracted with DCM
  2. concentrationThe organic phases were concentrated in vacuo
  3. customthe crude residue was purified by CC with EtOAc-Hept (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-908da1bc3303458a97e0e63b60158d7b
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202885B2

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