Dimethyl Sulfoxide → (4-Chloro-3-methyl-2-pyridyl)cyclopropylketone

Participants

Reaction Conditions

Reaction Steps

11.22 ml of oxalyl chloride was dissolved in 300 ml of anhydrous dichloromethane, and under cooling at −78° C., 100 ml of anhydrous dichloromethane solution of 9.83 ml of anhydrous dimethylsulfoxide was dropped thereto. The resulting mixture was stirred at −78° C. for 40 minutes, and thereafter, 200 ml of anhydrous dichloromethane solution of 19.55 g of (4-chloro-3-methyl-2-pyridyl)cyclopropylmethane-1-ol (IX) was dropped thereto. The resulting mixture was stirred at −78° C. for 30 minutes, and thereafter, the reaction temperature was elevated to −45° C. and the resulting mixture was stirred at the same temperature for 1 hour, and thereafter, 68.93 ml of triethylamine was dropped thereto and the temperature of the resulting mixture was elevated to a room temperature. Water was added thereto and the resulting mixture was extracted with chloroform, and the resulting organic layer was washed with water and saturated salt water, and thereafter, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; hexane: ethyl acetate=19:1) to obtain 17.89 g of (4-chloro-3-methyl-2-pyridyl)cyclopropylketone (X).

Provenance & Evidence