Chloroform → 1-(1,2-Oxazolidin-2-yl)-2-{4-[4-(trifluoromethyl)phenoxy]phenoxy}propan-1-one

HRID 543580

Reaktionsgleichung

Reaktionsgleichung von HRID 543580
Cl.[O:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.C(Cl)(Cl)Cl.[F:11][C:12]([F:33])([F:32])[C:13]1[CH:31]=[CH:30][C:16]([O:17][C:18]2[CH:29]=[CH:28][C:21]([O:22][CH:23]([CH3:27])[C:24](Cl)=[O:25])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1.C(N(CC)CC)C>O>[F:11][C:12]([F:32])([F:33])[C:13]1[CH:31]=[CH:30][C:16]([O:17][C:18]2[CH:29]=[CH:28][C:21]([O:22][CH:23]([CH3:27])[C:24]([N:3]3[CH2:4][CH2:5][CH2:6][O:2]3)=[O:25])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 12304500Isoxazolidine hydrochlorideHCID 129060152-{4-[4-(Trifluoromethyl)phenoxy]phenoxy}propanoyl chloride

Produkt 1

HCID 132794361-(1,2-Oxazolidin-2-yl)-2-{4-[4-(trifluoromethyl)phenoxy]phenoxy}propan-1-oneAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of isoxazolidine hydrochloride (11.0 g) and chloroform (200 ml), under stirring and ice-cooling, was added (±)-2-[4-(4-trifluoromethylphenoxy)phenoxy]propionyl chloride (34.5 g) and then added dropwise triethylamine (22.2 g). After the completion of addition, the reaction mixture was stirred for further 30 minutes at room temperature, to which water was added to form two layers. The organic layer so separated was washed with 1 N hydrochloric acid and then with 1 N aqueous sodium hydroxide and dried over anhydrous sodium sulfate. Removal of the solvent by a distillation in vacuo gave N-[(±)-2-[4-(4-trifluoromethylphenoxy)phenoxy]propionyl]isoxazolidine (37.3 g) as a white crystalline solid. After recrystallization from a mixture of n-hexane/acetone, the resulting white crystalline solid showed the melting point of 105°-107° C.

Aufarbeitung

  1. temperatureice-cooling
  2. additionAfter the completion of addition
  3. additionwas added
  4. customto form two layers
  5. customThe organic layer so separated
  6. washwas washed with 1 N hydrochloric acid
  7. dry with materialwith 1 N aqueous sodium hydroxide and dried over anhydrous sodium sulfate
  8. customRemoval of the solvent
  9. distillationby a distillation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a8959e1479f54b079121103f4d2ac70f
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04447259

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