Reaction equation
C(N(CC)[CH2:4][CH2:5][C:6](=[O:19])[CH2:7][CH:8]([CH3:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)C.CC(CC1C=CC=C(OC)C=1)CC(=O)C=C.[CH2:38]([CH:40]1[C:44](=[O:45])[CH2:43][CH2:42][C:41]1=[O:46])[CH3:39]>[OH-].[K+]>[CH2:38]([C:40]1([CH2:4][CH2:5][C:6](=[O:19])[CH2:7][CH:8]([CH3:18])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[C:44](=[O:45])[CH2:43][CH2:42][C:41]1=[O:46])[CH3:39]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Add a mixture of 1-diethylamino-6-(m-methoxyphenyl)-5-methylhexan-3-one and 5-methyl-6-(m-methoxyphenyl)hex-1-en-3-one (6 g, prepared by slow distillation of the former substance) to 2-ethylcyclopentane-1,3-dione (3.5 g) in 0.12% methanolic potassium hydroxide (10 cc) and heat the mixture under reflux for 16 hours. Remove most of the solvent under reduced pressure and add ether (25 cc) and benzene (25 cc) to the residue. Wash the solution with 5% aqueous sodium hydroxide, water, dilute hydrochloric acid, and brine, and dry. Evaporate the solvent to obtain a viscous brown gum, which is the triketone 2-ethyl-2-(6-m-methoxyphenyl-5-methyl-3-oxohexyl)cyclopentane-1,3-dione.
Workup
- additionAdd
- temperatureheat the mixture
- temperatureunder reflux for 16 hours
- customRemove most of the solvent under reduced pressure
- additionadd ether (25 cc) and benzene (25 cc) to the residue
- washWash the solution with 5% aqueous sodium hydroxide, water, dilute hydrochloric acid, and brine
- customdry
- customEvaporate the solvent
- customto obtain a viscous brown gum, which
Sources & evidence
- ORD record
- ord-f7f789b41872412795649383b740ece9
- Source dataset
- uspto-grants-1977_01
- Patent number
- US04002746
Linked notes
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