Hydrochloric Acid → Triphenylsulfonium difluoro-(2-hydroxyadamantan-2-yl)acetate

Participants

Reaction Steps

A mixture of 3.9 g of ethyl difluoro-(2-hydroxyadamantan-2-yl)acetate, prepared in Synthesis Example 1-8, 20 g of 1,4-dioxane, and 4.8 g of 25 wt % sodium hydroxide was stirred for 2 hours. To the reaction solution, 1.5 g of 35 wt % hydrochloric acid was added, and then 24 g of an aqueous solution of triphenylsulfonium chloride and 100 g of methylene chloride were added. After stirring for 30 minutes, the organic layer was taken out, washed with water, and concentrated under reduced pressure. Methyl isobutyl ketone was added to the concentrate, which was concentrated again. Diisopropyl ether was added to the concentrate for crystallization. The resulting solid was dried in vacuum, obtaining 4.7 g of the target compound, triphenylsulfonium difluoro-(2-hydroxyadamantan-2-yl)acetate as white crystals (yield 63%).

Provenance & Evidence