Fluorene → 2-(3-Tert-butyl-5-methylcyclopentadienyl)-2-fluorenylpropane

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Reaction Steps

To a solution of 10.1 g (60.8 mmol) of fluorene in 300 ml of THF, 40 ml (61.6 mmol) of a hexane solution of n-butyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for 5 hours (dark brown solution). The solution was ice cooled again, and a solution of 11.7 g (66.5 mmol) of 3-tert-butyl-1,6,6-trimethylfulvene in 300 ml of THF was dropwise added in a nitrogen atmosphere. After stirring at room temperature for 14 hours, the resulting brown solution was ice cooled, and 200 ml of water was added. The organic phase extracted with diethyl ether and separated was dried over magnesium sulfate and then filtered. From the filtrate, the solvent was removed under reduced pressure to obtain an orangy brown oil. The oil was purified by silica gel column chromatography (developing solvent: hexane) to obtain 3.8 g of a yellow oil. The analyzed values are given below.

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