Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.Cl([O-])(=O)(=O)=O.[Li+].Cl[C:17]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[O:18].O>[N+](C)([O-])=O.[O-]S(C(F)(F)F)(=O)=O.[Sc+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=1[C:17](=[O:18])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
4-Methylanisole (732 mg) was dissolved in nitromethane (30 ml) to prepare a solution. Anhydrous lithium perchlorate (3.8 g), methyl 7-chlorocarbonyl-heptanoate (1.28 ml), and scandium triflate (300 mg) were added to the solution, and the mixture was stirred at room temperature for 4 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give methyl 8-(2-methoxy-5-methylphenyl)-8-oxo-octanoate (992 mg, yield 57%).
Workup
- customto prepare a solution
- extractionthe mixture was extracted with ethyl acetate
- washThe ethyl acetate layer was then washed with water
- dry with materialwas dried over anhydrous sodium sulfate
- customThe solvent was removed by distillation under the reduced pressure
- customthe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-ad03cac5cb004447ad3c5fe4302f02d4
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07560558B2
Linked notes
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