Diethyl Ether → 1-(3,5-Dichloro-2-pyridyl)-3-trifluoromethylpropane-1,3-dione

HRID 650481

Reaction equation

HRID 650481 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[O:11])[CH3:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])(=O)C.CCOCC.C([O-])C.[Na+]>C(O)C>[Cl:1][C:2]1[C:3]([C:9](=[O:11])[CH2:10][C:16]([C:17]([F:20])([F:19])[F:18])=[O:15])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 1362562,2,2-Trifluoroethyl AcetateHCID 2723922Sodium ethoxideHCID 217121631-(3,5-Dichloropyridin-2-yl)ethanone

Product 1

HCID 217121521-(3,5-Dichloro-2-pyridyl)-3-trifluoromethylpropane-1,3-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15.8 g of 3,5-dichloro-2-acetylpyridine are introduced together with 12.0 ml of trifluoroethyl acetate into 125 ml of absolute ether. With stirring, the mixture is cooled using an ice-bath and 46.6 ml of, a 21% sodium ethanolate solution in ethanol are added dropwise. The ice-bath is then removed and the mixture is subsequently stirred overnight at 25° C. After cooling the reaction mixture in an ice-bath and adding dropwise 7.5 ml of glacial acetic acid, the mixture is concentrated in vacuo. 39.0 g of 1-(3,5-dichloro-2-pyridyl)-3-trifluoromethylpropane-1,3-dione are obtained, which can be used directly for the following cyclisation step.

Workup

  1. temperaturethe mixture is cooled
  2. customThe ice-bath is then removed
  3. temperatureAfter cooling the reaction mixture in an ice-bath
  4. additionadding dropwise 7.5 ml of glacial acetic acid
  5. concentrationthe mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-d48b8b86d8ba4b78b29c8927f41d80b5
Source dataset
uspto-grants-2001_08
Patent number
US06274536B1

Linked notes

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