Ethanol → 3-Ethoxy-1-(3-pyridinyl)-2-propen-1-one

HRID 1247954Notes

Reaction equation

HRID 1247954 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:6].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:25]([OH:27])[CH3:26]>>[CH2:25]([O:27][CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:6])[CH3:26]

Participants

4

Reactant 3

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one

Product 1

HCID 540323263-Ethoxy-1-(3-pyridinyl)-2-propen-1-one

Procedure

A mixture of 0.10 mole of 3-dimethylamino-1-(3-pyridinyl)-2-propen-1-one and 0.20 mole of p-toluenesulfonic acid in 150 ml of anhydrous ethanol was refluxed for 10 hours. The solvent was removed and the residue partitioned between water and dichloromethane. The organic layer was dried over magnesium sulfate and the solvent removed, giving 3-ethoxy-1-(3-pyridinyl)-2-propen-1-one.

Workup

  1. temperaturewas refluxed for 10 hours
  2. customThe solvent was removed
  3. customthe residue partitioned between water and dichloromethane
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent removed

Sources & evidence

ORD record
ord-64c5b816faa34d3e82a72f8bd2cc1385
Source dataset
uspto-grants-1985_06
Patent number
US04521422

Reaction notes

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