Water → HCID 19689334, compound

HRID 975208Notes

Reaction equation

HRID 975208 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.O.Cl[O-].[Ca+2].Cl[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 962Water2×HCID 24504Calcium hypochloriteHCID 199715826-(2,2,2-Trifluoroethoxy)-α-(trifluoromethyl)-3-pyridinemethanol

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 20 ml of methylene chloride at room temperature. After addition of 4 ml of water and 1.72 g (0.012 mol) of calcium hypochlorite the mixture is stirred for 4 hours with vigorous mixing, 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), 2.38 g (87% of theory) of 2-(2,2,2-trifluoroethoxy)-5-trifluoroacetylpyridine are obtained.

Workup

  1. customrises to 25 ° C
  2. customthe phases are separated
  3. extractionthe aqueous phase is extracted several times with methylene chloride
  4. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  5. dry with materialAfter drying the organic phase with sodium sulfate
  6. distillationthe volatiles are distilled off
  7. distillationdistillation of the crude product in a kugelrohr (0.3 mbar, 100°-120° C. bath temperature), 2.38 g (87% of theory) of 2-(2,2,2-trifluoroethoxy)-5-trifluoroacetylpyridine
  8. customare obtained

Sources & evidence

ORD record
ord-1244c8143d874d37a65d07391f132516
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Reaction notes

Loading…