Acetone → 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide
Reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[N:14][OH:15])[C:10]([NH:12][CH3:13])=[O:11].[C:16](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.CC(C)=O>O>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[N:14][O:15][CH3:16])[C:10]([NH:12][CH3:13])=[O:11]Participants
6
Procedure
A mixture of 2-(2-hydroxymethylphenyl)-2-hydroxyimino-N-methylacetamide (521 mg, E/Z≠93/7), potassium carbonate (415 mg), 95% dimethyl sulfate (365 mg) and acetone (5.0 ml) was stirred at room temperature for 6 hours. A few pieces of ice were added, and the mixture was stirred for 30 minutes. Water (about 50 ml) was added, and the mixture was extracted with ethyl acetate three times. The combined ethyl acetate layer was washed with saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave the crude product (E/Z≠9 97/3). The crude product was crystallized from ethyl acetate-hexane to obtain the title compound as crystals (389 mg) (E/Z=97/3, yield: 70.0%).
Workup
- additionA few pieces of ice were added
- stirringthe mixture was stirred for 30 minutes
- extractionthe mixture was extracted with ethyl acetate three times
- washThe combined ethyl acetate layer was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customEvaporation of the solvent under reduced pressure
- customgave the crude product (E/Z≠9 97/3)
- customThe crude product was crystallized from ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-a0d34b41a2a64017916e7ed953398fed
- Source dataset
- uspto-grants-2000_03
- Patent number
- US06037495
Reaction notes
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