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

HRID 1741820ノート

反応式

HRID 1741820 の反応式
[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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4691b586e8a44f428a25aaf904b438d0
出典データセット
uspto-grants-1994_08
特許番号
US05334716

反応ノート

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