Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → ethyl (4E)-5-(2-pyridyl)-4-pentenoate

HRID 1741820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1741820
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[CH:8]/[CH2:9][CH2:10][C:11]([OH:13])=[O:12].[CH3:14][C:15]1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[CH:8]/[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Komponenten

4

Edukt 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 19010766(4E)-5-(2-pyridyl)-4-pentenoic acid

Produkt 1

HCID 11217977ethyl (4E)-5-(2-pyridyl)-4-pentenoateAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of (4E)-5-(2-pyridyl)-4-pentenoic acid (1.6 g) in ethanol (50 ml) was added d-camphor-10-sulfonic acid (2.3 g), and the mixture was heated under reflux with a reflux condenser containing 3 Å molecular sieves. After 2 hours, the mixture was evaporated, diluted with saturated aqueous sodium bicarbonate and then extracted with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate and evaporated in vacuo to give ethyl (4E)-5-(2-pyridyl)-4-pentenoate (1.84 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux with a reflux condenser
  3. additioncontaining 3 Å molecular sieves
  4. customthe mixture was evaporated
  5. additiondiluted with saturated aqueous sodium bicarbonate
  6. extractionextracted with ethyl acetate
  7. washThe organic layers were washed with brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4691b586e8a44f428a25aaf904b438d0
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05334716

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