Hydrochloric Acid → 3,3-Difluoro-2-trifluoromethyl-2,3,3a,4,5,6,7,7a-octahydrobenzofuran-2,3a-diol

Participants

Reaction Conditions

Reaction Steps

In a nitrogen atmosphere at −5° C., 260 ml of 2.6M n-butyllithium in hexane was added to a mixture of 58 g of 1,1,1,3,3,3-hexafluoro-2-propanol and 260 g of tetrahydrofuran, followed by one hour of stirring at 5° C. Then 59 g of 2-bromocyclohexanone was added at 5° C. The mixture was stirred for 10 hours, after which dilute hydrochloric acid was added to quench the reaction and neutralize the reaction mixture. Then 310 g of a 10% aqueous solution of sodium hydroxide was added to the reaction mixture, from which an aqueous layer was separated. It was made acidic by adding 150 g of 20% dilute hydrochloric acid and combined with 250 g of toluene, after which separatory operation was performed to separate an organic layer. The organic layer was concentrated and purified by recrystallization from hexane, obtaining 58 g of the product (yield 72%).

Provenance & Evidence