Reaktionsgleichung
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([O:10][CH2:11][C:12]#[C:13][C:14]2[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:16][N:15]=2)[CH:3]=1.Cl.[NH2:30][OH:31].C([O-])(=O)C.[Na+]>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[N:30]/[OH:31])=[C:4]([O:10][CH2:11][C:12]#[C:13][C:14]2[C:18]([C:19]([F:21])([F:20])[F:22])=[C:17]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[O:16][N:15]=2)[CH:3]=1Komponenten
Versuchsvorschrift
A mixture of 4-bromo-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)prop-2-ynyloxy)benzaldehyde (Preparation 62D, 0.050 g, 0.111 mmol), hydroxylamine hydrochloride (9.26 mg, 0.133 mmol), and sodium acetate (0.018 g, 0.222 mmol) in methanol (2.0 mL) was heated at reflux for 30 min. The solvent was removed under reduce pressure, and the residue was diluted with dichloromethane, washed with water, and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded (E)-4-bromo-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)prop-2-ynyloxy)benzaldehyde oxime (0.050 g, 0.107 mmol, 97% yield) as a white solid. The product had an HPLC with a ret. time=3.26 min.−Column: Chromolith SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=466.8.
Aufarbeitung
- temperaturewas heated
- temperatureat reflux for 30 min
- customThe solvent was removed
- additionthe residue was diluted with dichloromethane
- washwashed with water
- dry with materialdried over anhydrous sodium sulfate
- concentrationConcentration under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-94b3a796633f4bb38f1b5aa9560f9d56
- Quelldatensatz
- uspto-grants-2015_12
- Patentnummer
- US09216972B2
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