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

HRID 1741820Notes

Reaction equation

HRID 1741820 reaction equation
[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]

Participants

4

Reactant 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

Product 1

HCID 11217977ethyl (4E)-5-(2-pyridyl)-4-pentenoateYield 99.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4691b586e8a44f428a25aaf904b438d0
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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