Potassium Carbonate → N-[(+/-)-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionyl]isoxazolidine

HRID 543583Notes

Reaction equation

HRID 543583 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[N:7][CH:8]=1.Cl[CH:20]([CH3:28])[C:21]([N:23]1[CH2:27][CH2:26][CH2:25][O:24]1)=[O:22].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:18][C:2]([F:1])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH:20]([CH3:28])[C:21]([N:23]3[CH2:27][CH2:26][CH2:25][O:24]3)=[O:22])=[CH:14][CH:15]=2)=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1552414-(5-Trifluoromethyl-pyridin-2-yloxy)-phenolHCID 133146162-Chloro-1-(isoxazolidin-2-yl)propan-1-one

Product 1

HCID 13314623N-[(+/-)-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionyl]isoxazolidineYield 92.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(5-trifluoromethyl-2-pyridyloxy)phenol (25.6 g), N-[(±)-2-chloropropionyl]isoxazolidine (16.4 g) which was prepared as in Example 1, anhydrous potassium carbonate (15.2 g) and acetonitrile (300 ml) was heated under reflux with stirring for 5 hours. After cooling, the reaction mixture was filtered through a suction filter to remove solid matters and the filtrate was concentrated in vacuo. The residue was washed with the addition of water and benzene and the organic layer formed was separated and dried over anhydrous sodium sulfate. The removal of the solvent by a distillation in vacuo gave N-[(±)-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionyl]isoxazolidine (35.5 g) as a pale yellow crystalline solid. Recrystallization from a mixture of n-hexane/ethyl acetate yielded a white crystalline solid. m.p. 83°-85° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through a suction
  5. filtrationfilter
  6. customto remove solid matters
  7. concentrationthe filtrate was concentrated in vacuo
  8. washThe residue was washed with the addition of water and benzene
  9. customthe organic layer formed
  10. customwas separated
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe removal of the solvent
  13. distillationby a distillation in vacuo

Sources & evidence

ORD record
ord-c720d9bfeb8142f68a0e1651442363a1
Source dataset
uspto-grants-1984_05
Patent number
US04447259

Reaction notes

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