Water → HCID 19689334, compound

HRID 975205Notes

Reaction equation

HRID 975205 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:16])[C:12]([F:15])([F:14])[F:13])=[CH:7][N:6]=1.Cl[O-].[Na+].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[F:18][C:2]([F:1])([F:17])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:16])[C:12]([F:13])([F:14])[F:15])=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 199715826-(2,2,2-Trifluoroethoxy)-α-(trifluoromethyl)-3-pyridinemethanolHCID 23665760Sodium Hypochlorite

Product 1

HCID 19689334HCID 19689334, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

43.15 g (0.157 mol) of 2-(2,2,2-trifluoroethoxy)-5-(2,2,2-trifluoro-1-hydroxyethyl)pyridine and 2.66 g (0.0078 mol) of tetrabutylammonium hydrogen sulfate are dissolved in 400 ml of ethyl acetate at room temperature. 240 ml (0.235 mol) of an approximately 6% strength sodium hypochlorite solution are metered in within 1 hour with vigorous stirring and the mixture is stirred for a further 2 hours during which the reaction temperature rises to 40° C. The reaction mixture is added to 500 ml of water, the phases are separated, the aqueous phase is extracted several times with ethyl acetate 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 (27 torr, 100°-102° C.), 24.47 g (57% of theory) of 2-(2,2,2-trifluoroethoxy)-5-trifluoroacetylpyridine are obtained, which, according to GC, is 97% pure.

Workup

  1. customare metered in within 1 hour
  2. stirringthe mixture is stirred for a further 2 hours during which the reaction temperature
  3. customrises to 40° C
  4. customthe phases are separated
  5. extractionthe aqueous phase is extracted several times with ethyl acetate
  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 (27 torr, 100°-102° C.), 24.47 g (57% of theory) of 2-(2,2,2-trifluoroethoxy)-5-trifluoroacetylpyridine
  10. customare obtained

Sources & evidence

ORD record
ord-2d977b88ca7748caab2ceafbb03a566c
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Reaction notes

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