Hydrochloric Acid → 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide
Reaction equation
CO.[OH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[N:16][O:17][CH3:18])[C:12]([NH:14][CH3:15])=[O:13].Cl.CON=C(C1C=CC=CC=1COC1CCCCO1)C(NC)=O>[Cl-].[Na+].O>[OH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[N:16][O:17][CH3:18])[C:12]([NH:14][CH3:15])=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Preparation of 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide Methanol (2 ml) and a 36% aqueous hydrochloric acid solution (0.01 g, 0.0001 mol) were added to an E/Z mixture of 2-methoxyimino-N-methyl-2-[2-(2-tetrahydropyranyloxymethyl)phenyl]acetamide (0.31 g, 0.001 mol), and the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, half-saturated brine (80 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 (0.21 g, Yield: 94.6%, E/Z=97/3) as colorless crystals.
Workup
- 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-d815929c9aa1476199258f8bb96ef56a
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05856573
Reaction notes
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