Hydrochloric Acid → HCID 86642238, compound

Participants

Reaction Steps

To a mixture of 2.1 g (5 mmol) of the triphenylsulfonium 3-hydroxypropanesulfonate prepared in Synthesis Example 1-14, 0.6 g (6 mmol) of triethylamine and 10 g of methylene chloride, 2.9 g (6 mmol) of 1-adamantanecarbonyl chloride was added dropwise, followed by stirring for 3 hours at room temperature. Then 5.5 g of 5% aqueous hydrochloric acid was added to quench the reaction. The organic layer was separated from the reaction solution, washed with water, and concentrated in vacuum. Methyl isobutyl ketone was added to the concentrate, which was concentrated in vacuum again while azeotroping off the residual water. Diisopropyl ether was added to the residue, followed by decantation and drying. There was obtained the target compound, triphenylsulfonium 3-(adamantane-1-carbonyloxy)propanesulfonate. Colorless oily matter, 2.3 g, yield 79%. The compound, designated PAG-5, has the following structure.

Provenance & Evidence