Reaction equation
Cl.[CH2:2]([O:4][NH2:5])[CH3:3].[OH-].[Na+].[OH:8][C:9]1[CH2:14][CH:13]([C:15]2[C:20]([CH3:21])=[C:19]([N+:22]([O-:24])=[O:23])[C:18]([CH3:25])=[C:17]([N+:26]([O-:28])=[O:27])[C:16]=2[CH3:29])[CH2:12][C:11](=[O:30])[C:10]=1[C:31](=O)[CH2:32][CH3:33]>C(O)C>[CH2:2]([O:4][N:5]=[C:31]([C:10]1[C:9](=[O:8])[CH2:14][CH:13]([C:15]2[C:16]([CH3:29])=[C:17]([N+:26]([O-:28])=[O:27])[C:18]([CH3:25])=[C:19]([N+:22]([O-:24])=[O:23])[C:20]=2[CH3:21])[CH2:12][C:11]=1[OH:30])[CH2:32][CH3:33])[CH3:3]Participants
Procedure
Ethoxyaminehydrochloride (0.36 g, 3.7 mmole) and then sodium hydroxide (0.15 g, 3.7 mmole) were added to a solution of 3-hydroxy-5-(2,4,6-trimethyl-3,5-dinitrophenyl)-2-propionylcyclohex-2-en-1-one (1.0 g; 2.7 mmole) in absolute ethanol (80 ml). The mixture was stirred at room temperature for a period of 24 hours and then the ethanol was removed by evaporation under reduced pressure. The residue was treated with dichloromethane and the organic phase was washed twice with water and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the product recrystallized from ethanol to give 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethyl-3,5-dinitrophenyl)cyclohex-2-en-1-one (0.45 g; 39.8%) as a white solid, mp 170° C.
Workup
- customthe ethanol was removed by evaporation under reduced pressure
- additionThe residue was treated with dichloromethane
- washthe organic phase was washed twice with water
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was removed by evaporation under reduced pressure
- customthe product recrystallized from ethanol
Sources & evidence
- ORD record
- ord-892533419a0649809487026e6043972a
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04666510
Linked notes
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