Hydrochloric Acid → 1-(Bicyclo[2.2.1]hept-5-en-2-yl)-2,2,4,4,4-pentafluorobutane-1,3,3-triol

Participants

Reaction Conditions

Reaction Steps

1290 mL of butyllithium (1.6 M hexane solution) was added to a mixture of 168 g of 1,1,1,3,3,3-hexafluoro-2-propanol and 1200 g of tetrahydrofuran at −70° C. under a nitrogen atmosphere. The temperature was increased to 0° C. gradually, and stirred at the temperature for 30 minutes. Then, 134 g of 5-norbornene-2-carbaldehyde was added thereto at 0° C. After stirring for 1 hour, dilute hydrochloric acid was added to terminate the reaction and to neutralize it. After the standard aqueous work-up, the product was purified by silica gel column chromatography to yield 230 g of 1-(5-norbornene-2-yl)-2,2,4,4,4-pentafluorobutane-1,3,3-triol (yield from 1,1,1,3,3,3-hexafluoro-2-propanol was 80%)

Provenance & Evidence