反应详情

温度

-78 °C

A mixture 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 was cooled to -78° C. Oxygen-containing ozone was bubbled into the mixture while stirring until the reaction mixture was colored blue. Then, nitrogen gas was bubbled into the blue reaction mixture to remove the excess ozone. Thereafter, 5 ml of dimethyl sulfide was added thereto. The resulting mixture was heated to room temperature. The reaction mixture, after having been allowed to stand for one day, was concentrated under reduced pressure. 20 Milliliters of acetone, 2 ml of water and 0.2 g of p-toluenesulfonic acid monohydrate were added to the resultant residue. The resulting reaction mixture, after having been allowed to stand at room temperature for 2 hours, was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=10/1) to obtain 0.98 g (yield: 82%) of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-3-formyl-2,2-dimethyl-cyclopropanecarboxylate, m.p. 43.2° C.

1. customwas bubbled into the mixture
2. customThen, nitrogen gas was bubbled into the blue reaction mixture
3. customto remove the excess ozone
4. additionThereafter, 5 ml of dimethyl sulfide was added
5. temperatureThe resulting mixture was heated to room temperature
6. concentrationwas concentrated under reduced pressure
7. addition20 Milliliters of acetone, 2 ml of water and 0.2 g of p-toluenesulfonic acid monohydrate were added to the resultant residue
8. customThe resulting reaction mixture
9. waitto stand at room temperature for 2 hours
10. extractionextracted with diethyl ether
11. dry with materialThe organic layer was dried over anhydrous sodium sulfate
12. concentrationconcentrated under reduced pressure
13. customThe resultant residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=10/1)