1-Propanol → 2-(2,5-dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone O-methyloxime
Reaction equation
C(O)CC.Cl.[CH3:6][O:7][NH2:8].[O:9]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][O:23][C:24]2[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=2[CH3:31])=O)=[N:10]1>O>[CH3:6][O:7][N:8]=[C:14]([C:11]1[CH:12]=[CH:13][O:9][N:10]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][O:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=1[CH3:31]Participants
5
Procedure
n-Propanol (2 ml) and methoxyamine hydrochloride (0.50 g, 6 mmol) were added to 2-(2,5-dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone (0.64 g, 2 mmol), and the mixture was stirred under reflux for 17 hours. After completion of the reaction, water (100 ml) was added, the mixture was extracted with dichloromethane. The dichloromethane layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel chromatography (benzene/n-hexane) to give 2-(2,5-dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone O-methyloxime (a mixture of isomers A/B) (0.55 g, 81.8%) as colorless crystals. mp. 104-108° C.
Workup
- temperatureunder reflux for 17 hours
- additionwas added
- extractionthe mixture was extracted with dichloromethane
- dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customthe residue was purified by silica gel chromatography (benzene/n-hexane)
Sources & evidence
- ORD record
- ord-035a1d70470e4bf191150b14f7a977cc
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06048885
Reaction notes
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