Methanol → 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide
Reaction equation
CO.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(OC([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33](=[N:38][O:39][CH3:40])[C:34]([NH:36][CH3:37])=[O:35])C)C>[Cl-].[Na+].O>[OH:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33](=[N:38][O:39][CH3:40])[C:34]([NH:36][CH3:37])=[O:35]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Methanol (4 ml) and pyridinium p-toluenesulfonate (0.04 g, 0.00017 mol) were added to an E/Z mixture of 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-2-methoxyimino-N-methylacetamide (0.50 g, 0.0017 mol), and the mixture was stirred under reflux for 2 hours. After completion of the reaction, half-saturated brine (100 ml) was added, and the mixture was extracted with dichloromethane (50 ml) twice. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide (0.34 g, Yield: 90.0%, E/Z=96/4) as a colorless oil.
Workup
- temperatureunder reflux for 2 hours
- additionwas added
- extractionthe mixture was extracted with dichloromethane (50 ml) twice
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
Sources & evidence
- ORD record
- ord-125ffc03e32f4c31badab379434a35ee
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05856573
Reaction notes
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