Water → HCID 19689334, compound

HRID 975204Notes

Reaction equation

HRID 975204 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(Cl)Cl>[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 6344DichloromethaneSolvent

Procedure

2.75 g (0.01 mol) of 2-(2,2,2-trifluoroethoxy)-5-(2,2,2-trifluoro-1-hydroxyethyl)pyridine and 0.18 g (0.0005 mol) of tetrabutylammonium hydrogen sulfate are dissolved in 30 ml of methylene chloride at room temperature. 22 ml (0.036 mol) of an approximately 12% strength sodium hypochlorite solution are metered in within 10 minutes with vigorous stirring and the mixture is stirred for a further 4.5 hours during which the reaction temperature rises to 25° C. The reaction mixture is added to 50 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 in a kugelrohr (0.3 mbar, 100°-120° C. bath temperature), 2.48 g (90% of theory) of 2-(2,2,2-trifluoroethoxy)-5-trifluoroacetylpyridine are obtained, which, according to GC, is 96% pure. nD20 : 1.4312.

Workup

  1. customare metered in within 10 minutes
  2. stirringthe mixture is stirred for a further 4.5 hours during which the reaction temperature
  3. customrises to 25° 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 in a kugelrohr (0.3 mbar, 100°-120° C. bath temperature), 2.48 g (90% of theory) of 2-(2,2,2-trifluoroethoxy)-5-trifluoroacetylpyridine
  10. customare obtained

Sources & evidence

ORD record
ord-f8126f82640f450092fdcdee3ec00db8
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Reaction notes

Loading…