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0 °C

A reaction vessel equipped with a dropping funnel was charged with 40 ml of dehydrated tetrahydrofuran and 2.35 g (6.08 mmol) of octamethyloctahydrodibenzofluorene synthesized by a method described in (i) of Synthetic Example 1 under nitrogen atmosphere, and 4.62 ml (7.30 mmol) of a hexane solution of n-butyllithium of 1.58 mol/L was added dropwise and stirred while cooling the above solution at 0° C. 1,3-Dimethyl-2-imidazolidinone 0.86 ml (7.90 mmol) was added to the above solution and stirred for 30 minutes. Then, a solution prepared by dissolving 2.00 g (6.68 mmol) of 6,6-di(p-chlorophenyl)fulvene in 30 ml of dehydrated tetrahydrofuran was [put] placed in the dropping funnel and added dropwise while cooling at −78° C., and the solution was stirred for one day while slowly allowing it to return to room temperature. This reaction solution was extracted with diethyl ether, and the separated organic layer was washed with 1N hydrochloric acid, a saturated sodium hydrogen carbonate aqueous solution and a saturated salt solution and dried over anhydrous magnesium sulfate. Then, magnesium sulfate was removed by filtration, and the solvent contained in the filtrate was removed by distillation under reduced pressure by means of a rotary evaporator. The residue was purified through a silica gel column and then recrystallized from toluene to obtain a targeted product (amount obtained: 0.714 g, yield: 17%). The targeted product was identified by means of 1H-NMR and FD-MS spectra.

1. customA reaction vessel equipped with a dropping funnel
2. customsynthesized by a method
3. stirringstirred for 30 minutes
4. customThen, a solution prepared
5. additionadded dropwise
6. temperaturewhile cooling at −78° C.
7. stirringthe solution was stirred for one day
8. customto return to room temperature
9. extractionThis reaction solution was extracted with diethyl ether
10. washthe separated organic layer was washed with 1N hydrochloric acid
11. dry with materiala saturated sodium hydrogen carbonate aqueous solution and a saturated salt solution and dried over anhydrous magnesium sulfate
12. customThen, magnesium sulfate was removed by filtration
13. customwas removed by distillation under reduced pressure by means of a rotary evaporator
14. customThe residue was purified through a silica gel column
15. customrecrystallized from toluene
16. customto obtain
17. customa targeted product (amount obtained: 0.714 g, yield: 17%)