Trifluoroacetic anhydride → Triphenylsulfonium 2-(adamantane-1-carbonyloxy)ethanesulfonate

Beteiligte Stoffe

Reaktionsschritte

In 125 g of trifluoroacetic acid were dissolved 14.8 g (0.10 mole) of sodium isethionate and 18.0 g (0.10 mole) of 1-adamantanecarboxylic acid. To this solution, 32.0 g (0.15 mole) of trifluoroacetic anhydride was added dropwise, followed by stirring for 2 hours at room temperature. Then 430 g (0.15 mole) of an aqueous solution of triphenylsulfonium chloride prepared in Synthesis Example 1-1, 800 g of water, and 1,500 g of methylene chloride were added, followed by stirring for 1 hour at room temperature. At the end of stirring, the organic layer was taken out, aqueous sodium bicarbonate was added dropwise until the pH of the aqueous layer ceased to be acidic, and the organic layer was then taken out. The organic layer was washed with water and concentrated in vacuum. Methyl isobutyl ketone was added to the concentrate, which was concentrated in vacuum again while distilling off the residual water. Diisopropyl ether was added to the residue for recrystallization. The crystals were collected and dried, obtaining the target compound, triphenylsulfonium 2-(adamantane-1-carbonyloxy)ethanesulfonate. White crystals, 34.1 g, yield 62%. The compound, designated PAG-1, has the following structure.

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