Methanol → HCID 53990473, compound
Reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][O:16][CH:17]([O:19][CH2:20][CH3:21])[CH3:18])=O)[CH:3]=1.CO.Cl.[CH3:25][O:26][NH2:27].C[O-].[Na+].CO>[Cl-].[Na+].O>[CH3:25][O:26][N:27]=[C:7]([C:4]1[CH:3]=[C:2]([CH3:1])[O:6][N:5]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][CH:17]([O:19][CH2:20][CH3:21])[CH3:18]Participants
6
Procedure
2-(1-Ethoxyethyl)oxymethylphenyl 5-methylisoxazol-3-yl ketone (4.34 g, 0.015 mol) was added to a mixture of methanol (30 ml), methoxyamine hydrochloride (2.51 g, 0.03 mol) and 28% sodium methylate/methanol solution (7.23 g, 0.0375 mol), and the mixture was stirred under reflux for 3 hours. After completion of the reaction, half-saturated brine (200 ml) was added, and the mixture was extracted with dichloromethane (100 ml) twice. The extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(1-ethoxyethyl)oxymethylphenyl 5-methylisoxazol-3-yl ketone O-methyloxime (4.32 g, yield: 90.5%) as a colorless oil.
Workup
- temperatureunder reflux for 3 hours
- additionwas added
- extractionthe mixture was extracted with dichloromethane (100 ml) twice
- dry with materialThe extracts were dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
Sources & evidence
- ORD record
- ord-96fd68893a7d489492969a6f878a3dc3
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06268312B1
Reaction notes
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