Water → 6-Fluoro-3-(3-methoxy-phenyl)-benzo[d]isoxazole

HRID 852079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852079
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)=[N:10][OH:11].CC(C)([O-])C.[K+].C(OCC)(=O)C.O>O1CCCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)=[N:10][O:11][C:2]=2[CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 72465824(2,4-Difluoro-phenyl)-(3-methoxy-phenyl)-methanone oxime

Produkt 1

HCID 179062626-Fluoro-3-(3-methoxy-phenyl)-benzo[d]isoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Cool (2,4-difluoro-phenyl)-(3-methoxy-phenyl)-methanone oxime (52.66 g, 217 mmol) in tetrahydrofuran (500 mL) to 0° C. Add 1.0 M solution of potassium tert-butoxide in tetrahydrofuran (260 mL, 0.26 mol) and stir at room temperature for 1.5 hours. Reflux reaction mixture for an additional 1.5 hours. Cool to room temperature overnight. Dilute reaction mixture with ethyl acetate and water and separate. Dry the organic layer and concentrate to give the title compound as an oil. Purify by column chromatography (dichloromethane) and triturate with pentane to give the title compound as a white solid (30.2 g, 62% Yield). NMR and M/S are consistent with the final, desired compound. mp=68-69° C.

Aufarbeitung

  1. temperatureReflux
  2. customreaction mixture for an additional 1.5 hours
  3. temperatureCool to room temperature overnight
  4. additionDilute
  5. customseparate
  6. customDry the organic layer
  7. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-d23042a69e9341eaacf5cf25b1c49686
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253165B2

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