Methanol → (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-3-formyl-2,2-dimethylcyclopropanecarboxylate

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence