反应详情

Into a mixture solution of 1.27 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate, 20 ml of methanol and 20 ml of ethyl acetate, oxygen containing ozone was blown at −78° C. until the color of the solution was changed to blue. Then nitrogen gas was blown into the solution for removing excess ozone, 5 ml of dimethylsulfide was added to the solution and the solution was brought to room temperature. After one day, the reaction solution was concentrated under reduced pressure. To the residue, 20 ml of acetone, 2 ml of water and 0.2 g of p-toluenesulfonic acid monohydrate were added and allowed to stand at room temperature for 2 hours. The reaction solution was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue, which was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=10/1) to give 0.98 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-3-formyl-2,2-dimethylcyclopropanecarboxylate (yield 82%). m.p. 43.2° C.

1. customwas blown at −78° C. until the color of the solution
2. customfor removing excess ozone, 5 ml of dimethylsulfide
3. additionwas added to the solution
4. customwas brought to room temperature
5. concentrationthe reaction solution was concentrated under reduced pressure
6. additionTo the residue, 20 ml of acetone, 2 ml of water and 0.2 g of p-toluenesulfonic acid monohydrate were added
7. waitto stand at room temperature for 2 hours
8. additionThe reaction solution was poured into water
9. extractionextracted with diethyl ether
10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
11. concentrationconcentrated under reduced pressure
12. customto give a residue, which