Chloride → HCID 86695367, compound

Participants

Reaction Steps

3-Cyclohexenecarbonyl chloride prepared by reaction of 4.2 g (0.03 mole) of 3-cyclohexenecarboxylic acid with 5.1 g (0.04 mole) of oxalyl chloride was dissolved in 12 g of methylene chloride. A solution of 3-cyclohexenecarbonyl chloride in methylen chloride, as prepared above, was added dropwise to a mixed solution of 15 g (0.03 mole) of triphenylsulfonium 1,1,3,3,3-pentafluoro-2-hydroxypropane-1-sulfonate prepared in accordance with the method described in Japanese Patent Laid-Open Publication No. 2007-145804, 2.4 g (24 millimoles) of triethylamine, 0.1 g (1 millimole) of N,N′-dimethylaminopyridine, and 60 g of methyle chloride. The mixture was then stirred at room temperature for 5 hours. After stirring, 30 g of 5% dilute hydrochloric acid was added to quench the reaction. An organic layer was isolated and washed with water. After washing with water, the organic layer was concentrated. To the organic layer, methyl isobutyl ketone was added, and the mixture was washed with water. After then, the washed organic layer was concentrated, and diisopropyl ether was added to perform recrystallization. The crystal was filtered off, collected, and dried under reduced pressure at 50° C. to obtain 14 g of triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(3-cyclohexenecarbonyloxy)propane-1-sulfonate (PAG intermediate) which was a target compound as a white crystal (yield: 78%).

Provenance & Evidence