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

In a nitrogen atmosphere at −70° C., 1290 ml of 1.6M n-butyllithium in hexane was added to a mixture of 168 g of 1,1,1,3,3,3-hexafluoro-2-propanol and 1200 g of tetrahydrofuran. The mixture was allowed to warm up slowly to 0° C. and stirred at the temperature for 30 minutes. Then 134 g of 5-norbornene-2-carboxaldehyde was added at 0° C. The mixture was stirred for 1 hour, after which dilute hydrochloric acid was added to quench the reaction and neutralize the reaction mixture. This was followed by conventional aqueous work-up and purification by silica gel column chromatography, collecting 230 g of 1-(5-norbornen-2-yl)-2,2,4,4,4-pentafluorobutane-1,3,3-triol (yield 80% based on the 1,1,1,3,3,3-hexafluoro-2-propanol).

Provenance & Evidence