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

HRID 1741820노트

반응식

HRID 1741820 반응식
[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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4691b586e8a44f428a25aaf904b438d0
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05334716

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