Ammonium Chloride → Ethyl 2,2-dimethyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-cyclopropane carboxylate
Reaction equation
[CH3:1][C:2]1([CH3:22])[CH:4]([CH:5](OC(=O)C)[C:6](Cl)([Cl:11])[C:7]([F:10])([F:9])[F:8])[CH:3]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[Cl-].[NH4+]>CN(C=O)C.[Zn]>[CH3:1][C:2]1([CH3:22])[CH:4]([CH:5]=[C:6]([Cl:11])[C:7]([F:8])([F:9])[F:10])[CH:3]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 183 mg (0.500 mmol) of ethyl 2,2-dimethyl-3-(1-acetoxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate obtained in Example 9, in 0.5 ml of DMF, 35 mg (0.54 mmol) of zinc powder was added, and the mixture was stirred at 50° C. for 4 hours. After an addition of 1 ml of a saturated ammonium chloride aqueous solution, the mixture was extracted with diethyl ether (1 ml×5 times). The extract was dried over anhydrous magnesium sulfate, then filtered and concentrated under reduced pressure. The product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=1/3) to obtain 116 mg of ethyl 2,2-dimethyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-cyclopropane carboxylate as a colorless oil.
Workup
- extractionthe mixture was extracted with diethyl ether (1 ml×5 times)
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=1/3)
Sources & evidence
- ORD record
- ord-1c510f70529049bd9e5085c81ff281d5
- Source dataset
- uspto-grants-1989_09
- Patent number
- US04864052
Reaction notes
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