Methyl p-toluenesulfonate → 3-(3-Hydroxy-1-propenyl)-1-methylpyridinium p-toluenesulfonate

HRID 2081513Notes

Reaction equation

HRID 2081513 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][CH2:9][OH:10])[CH:2]=1.[C:11]1([CH3:22])[CH:16]=[CH:15][C:14]([S:17]([O:20]C)(=[O:19])=[O:18])=[CH:13][CH:12]=1>CC(C)=O>[C:11]1([CH3:22])[CH:12]=[CH:13][C:14]([S:17]([O-:20])(=[O:18])=[O:19])=[CH:15][CH:16]=1.[OH:10][CH2:9][CH:8]=[CH:7][C:3]1[CH:2]=[N+:1]([CH3:11])[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 35635042-Propen-1-ol, 3-(3-pyridinyl)-

Product 1

HCID 867442753-(3-Hydroxy-1-propenyl)-1-methylpyridinium p-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 3-(3-pyridyl)acrylate was reduced using lithium aluminum hydride to give 3-(3-pyridyl)-2-propen-1-ol. In 30 ml of acetone 710 mg of 3-(3-pyridyl)-2-propen-1-ol and 980 mg of methyl p-toluenesulfonate were heated under reflux for 22 hours. The reaction mixture was subjected by decantation to remove the solvent and then washed with acetone and ether. The residue was dried under reduced pressure to give 1.3 g of the desired compound as an orange-colored oil.

Workup

  1. temperatureunder reflux for 22 hours
  2. customto remove the solvent
  3. washwashed with acetone and ether
  4. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-34c8cf0ef2554d788a91ee65d4ccc56c
Source dataset
uspto-grants-1993_02
Patent number
US05183811

Reaction notes

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