Fluorene → 2,3,4,9-Tetrahydro-1H-fluorene

Participants

Reaction Steps

15 g (90.2 mmol) of fluorene was dissolved in 200 ml of a tetrahydrofuran (THF)/ethylene diamine solution (1:1 ratio). The solution was cooled in a ice bath and with stirring 3.13 g of lithium (451.2 mmol) was added in small portions. After all the lithium had been added the solution was stirred for 2 h with consequent dissolution of the lithium metal. The resulting solution was then poured into a HCl/ice mixture. The solution was then extracted with diethyl ether. The organic washings were combined, washed with water and dried over MgSO4. The solution was filtered and the solvent removed on a rotary evaporator. The crude material was then purified by dissolving in hexane and passing through a silica gel column to give 11.4 g (75 percent yield) of product after solvent removal.

Provenance & Evidence