Water → 2,2,2-trifluoro-1-(pyridin-3-yl)ethanone

HRID 975216Notes

Reaction equation

HRID 975216 reaction equation
[F:1][C:2]([F:12])([F:11])[CH:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[OH:4].Cl[O-].[Na+].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[F:12][C:2]([F:1])([F:11])[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 112175572,2,2-Trifluoro-1-(pyridin-3-yl)ethanolHCID 23665760Sodium Hypochlorite

Product 1

HCID 117690612,2,2-trifluoro-1-(pyridin-3-yl)ethanone

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

13.2 g (0.075 mol) of 2,2,2-trifluoro-1-(3-pyridyl)ethanol and 1.26 g (0.0037 mol) of tetrabutylammonium hydrogen sulfate are dissolved in 250 ml of methylene chloride at room temperature. 46 ml (0.09 mol) of an approximately 12% strength sodium hypochlorite solution are metered in within 20 minutes with vigorous stirring and the mixture is stirred for a further 4 hours during which the reaction temperature rises to 35° C. The reaction mixture is added to 250 ml of water, the phases are separated, the aqueous phase is extracted several times with methylene chloride and the combined organic phases are washed with saturated aqueous sodium chloride solution. After drying the organic phase with sodium sulfate, the volatiles are distilled off. Following distillation of the crude product (28 torr, 65°-70°C.), 9.39 g (72% of theory) of 3-trifluoroacetylpyridine are obtained. nD20 : 1.4796.

Workup

  1. customare metered in within 20 minutes
  2. stirringthe mixture is stirred for a further 4 hours during which the reaction temperature
  3. customrises to 35° C
  4. customthe phases are separated
  5. extractionthe aqueous phase is extracted several times with methylene chloride
  6. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  7. dry with materialAfter drying the organic phase with sodium sulfate
  8. distillationthe volatiles are distilled off
  9. distillationdistillation of the crude product (28 torr, 65°-70°C.), 9.39 g (72% of theory) of 3-trifluoroacetylpyridine
  10. customare obtained

Sources & evidence

ORD record
ord-7e240e5ae1574e518d9fe65fd153338a
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Reaction notes

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