Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:9][CH2:10][CH2:11]Cl)=[CH:4][CH:3]=1.[NH:20]1[CH2:30][CH2:29][CH:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+]>[I-].[K+].C(C(C)=O)C(C)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:9][CH2:10][CH2:11][N:20]2[CH2:30][CH2:29][CH:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:22][CH2:21]2)=[CH:4][CH:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
1.43 g of 1-bis(4-fluorophenyl)methoxy-2-chloroethane and 1.00 g of ethyl isonipecotate were added to 10 ml of methyl isobutyl ketone, and the reaction mixture was then heated under reflux for 5 hours together with 2.0 g of sodium carbonate and 10 mg of potassium iodide. At the end of this time, the mixture was filtered and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography. Elution with a 3:1 by volume mixture of hexane and ethyl acetate afforded 1.45 g (yield 71%) of the title compound as an oily substance.
Workup
- temperaturethe reaction mixture was then heated
- filtrationAt the end of this time, the mixture was filtered
- customthe solvent was removed by distillation under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
- washElution with a 3:1
- additionby volume mixture of hexane and ethyl acetate
Sources & evidence
- ORD record
- ord-2ba6eac6083142daa3daa7b78ecf6525
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05294623
Linked notes
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