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

HRID 543583ノート

反応式

HRID 543583 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c720d9bfeb8142f68a0e1651442363a1
出典データセット
uspto-grants-1984_05
特許番号
US04447259

反応ノート

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