Trifluoroacetic acid → Rac-6-chloro-3-(3,5-dimethoxy-phenyl)-1,3-dihydro-indol-2-one
Reaktionsgleichung
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=3)(O)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
Crude rac-6-chloro-3-(3,5-dimethoxy-phenyl)-3-hydroxy-1,3-dihydro-indol-2-one (0.3 g, 0.94 mmol) (from Example 40a supra) was suspended in a mixture of triethylsilane (0.45 mL, 2.82 mmol) (Aldrich) and trifluoroacetic acid (1.38 g, 14.1 mmol) and heated in an 90° C. oil bath for 17 hours. After cooling to room temperature, mixture was diluted with ethyl acetate and treated with solid sodium carbonate (1 g). After stirring for 30 minutes, mixture was extracted with water and brine. Aqueous layers were back washed with ethyl acetate. Organic layers were combined, dried (Na2SO4), filtered and concentrated. Residue was recrystallized from dichloromethane-hexanes to give rac-6-chloro-3-(3,5-dimethoxy-phenyl)-1,3-dihydro-indol-2-one as yellow solid. (Yield 0.2 g, 71%)
Aufarbeitung
- temperatureAfter cooling to room temperature
- extractionmixture was extracted with water and brine
- washAqueous layers were back washed with ethyl acetate
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customResidue was recrystallized from dichloromethane-hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-412eb060f4ae4f9ab85c5a1e5558430d
- Quelldatensatz
- uspto-grants-2009_08
- Patentnummer
- US07576082B2
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