2-Methylpyridine → 1-(2-Cyclopent-1-enyl-2-oxo-ethyl)-2-methyl-pyridinium bromide salt

HRID 37822

Reaction equation

HRID 37822 reaction equation
[Br:1][CH2:2][C:3]([C:5]1(Br)[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17]>CC(C)=O>[Br-:1].[C:5]1([C:3](=[O:4])[CH2:2][N+:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH2:9][CH2:8][CH2:7][CH:6]=1

Participants

4

Reactant 2

HCID 79752-MethylpyridineHCID 124665932-Bromo-1-(1-bromo-cyclopentyl)-ethanone

Product 1

HCID 866395941-(2-Cyclopent-1-enyl-2-oxo-ethyl)-2-methyl-pyridinium bromide saltYield 117.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Bromo-1-(1-bromo-cyclopentyl)-ethanone (3.7 g, 13.7 mmol) and α-picoline (1.02 g, 11.0 mmol) in acetone were heated at reflux overnight. The reaction mixture was allowed to cool then concentrated in vacuo. The crude mass was washed with 30% ethyl acetate/petroleum ether and diethyl ether. 1-(2-Cyclopent-1-enyl-2-oxo-ethyl)-2-methyl-pyridinium bromide salt (3.65 g, 94%) was obtained as a semi-solid material and taken for next step without purification.

Workup

  1. temperatureat reflux overnight
  2. temperatureto cool
  3. concentrationthen concentrated in vacuo
  4. washThe crude mass was washed with 30% ethyl acetate/petroleum ether and diethyl ether

Sources & evidence

ORD record
ord-c29a18fee9b8430f971d96da9a294c69
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Linked notes

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