反应详情

After 233 g of 1-(2,2,2-trifluoroethoxy)naphthalene synthesized in Synthesis Example 1-2 was dispersed in 462 g of Eaton's reagent (diphosphorus pentaoxide-methanesulfonic acid solution) available from Sigma-Aldrich Co., LLC, and 104 g of tetramethylene sulfoxide was added dropwise under ice-cooling and mixed. Aging was carried out at room temperature overnight, 700 g of water and 600 g of diisopropyl ether were added to the mixture under ice-cooling, and the aqueous layer was collected by separation. The aqueous layer was again washed with 600 g of diisopropyl ether, to prepare 4-(2,2,2-trifluoroethoxy)-1-naphthyltetrahydrothiophenium=methanesulfonate as an aqueous solution. To 590 g (corresponding to 0.39 mol) of the aqueous solution were added 160 g of triethyl ammonium=2-(adamantane-1-carbonyloxy)-3,3,3-trifluoro-2-trifluoromethylpropane-1-sulfonate synthesized in Synthesis Example 1-1, 1000 g of methylene chloride and 200 g of water, and the organic layer was extracted from the mixed solution. The extracted organic layer was washed and then concentrated, methyl isobutyl ketone was added to the concentrate, and the mixture was again concentrated. Diisopropyl ether was added to the concentrated solution for recrystallization, and the deposited solid was recovered and dried under reduced pressure to obtain 209 g of 4-(2,2,2-trifluoroethoxy)-1-naphthyltetrahydrothiophenium=2-(adamantane-1-carbonyloxy)-3,3,3-trifluoro-2-trifluoromethylpropane-1-sulfonate (Yield: 93%) which is an objective product as a white solid.

1. temperaturecooling
2. additionmixed
3. temperaturecooling
4. customthe aqueous layer was collected by separation
5. washThe aqueous layer was again washed with 600 g of diisopropyl ether
6. customto prepare 4-(2,2,2-trifluoroethoxy)-1-naphthyltetrahydrothiophenium=methanesulfonate as an aqueous solution
7. extractionthe organic layer was extracted from the mixed solution
8. washThe extracted organic layer was washed
9. concentrationconcentrated
10. additionmethyl isobutyl ketone was added to the concentrate
11. concentrationthe mixture was again concentrated
12. additionDiisopropyl ether was added to the concentrated solution for recrystallization
13. customthe deposited solid was recovered
14. customdried under reduced pressure