Ethylene Glycol → 4-Chloro-2-(2-methyl-1,3-dioxolan-2-yl)pyridine

HRID 333061Notes

Reaction equation

HRID 333061 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](=[O:10])[CH3:9])[CH:3]=1.[CH2:11](O)[CH2:12][OH:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2([CH3:9])[O:13][CH2:12][CH2:11][O:10]2)[CH:3]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 130119861-(4-Chloro-pyridin-2-yl)-ethanone

Product 1

HCID 668355144-Chloro-2-(2-methyl-1,3-dioxolan-2-yl)pyridineYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(4-Chloro-2-pyridyl)ethanone (440 mg, 2.83 mmol) and ethyleneglycol (480 mg, 3 mmol) were mixed with toluene (10 ml), a catalytic amount of p-toluenesulfonic acid was added and the mixture was heated at reflux overnight. The mixture was evaporated to dryness to yield 523 mg of a solid (2.6 mmol, 93%). MS (APCI) m/z=200.0 [M+H]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. customThe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-faee9a2986ae4126a0a32cb0eb91dd6a
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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