Reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11]C)=[C:5]([CH3:13])[C:4]=1[CH:14]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].[N+]([O-])([O-])=O.[NH4+].[Ce].C(=O)([O-])O.[Na+]>C(#N)C.O>[CH3:13][C:5]1[C:6](=[O:11])[C:7]([CH3:10])=[C:8]([CH3:9])[C:3](=[O:2])[C:4]=1[CH:14]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The solution of 400 mg (1.12 mmol) of 5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-(3-pyridyl)pentanoic acid in 8 ml of acetonitrile-water (1:1) was cooled to 0° C., to which the solutioin of 1.55 g (2.82 mmol) of cerium ammonium nitrate in 6 ml of acetonitrile-water (1:1) was added with stirring. The reaction mixture was stirred for 30 minutes, neutralized with sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was washed with water and dried, and the solvent was evaporated off. The residue was purified with silica gel column (ethyl acetate), and recrystallized from ethanol, to give 200 mg (54.3%) of 5-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-5-(3-pyridyl)pentanoic acid.
Workup
- additionwas added
- stirringThe reaction mixture was stirred for 30 minutes
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- customdried
- customthe solvent was evaporated off
- customThe residue was purified with silica gel column (ethyl acetate)
- customrecrystallized from ethanol
Sources & evidence
- ORD record
- ord-15f93995daf94cd496322b947b43e577
- Source dataset
- uspto-grants-1989_07
- Patent number
- US04851413
Linked notes
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