反应详情

A 200-ml two-necked flask equipped with a magnetic stirrer, a three-way cock and a 100-ml dropping funnel was thoroughly purged with nitrogen, and sequentially charged with 1.35 g (3.48 mmol) of octamethyloctahydrodibenzofluorene and 40 mL of tetrahydrofuran. Then, 2.30 ml (3.60 mmol) of a 1.58 mol/l n-butyllithium/hexane solution was gradually added while cooling the mixture in an ice water bath, and then the mixture was stirred at room temperature for 20 hours under a nitrogen atmosphere. Subsequently, 1.18 g (3.57 mmol) of 6,6-di-2-naphthylfulvene dissolved in 30 ml of tetrahydrofuran in advance was gradually added over 30 minutes while cooling the mixture in a methanol/dry ice bath. The mixture was gradually warmed to room temperature, and stirred for 20 hours at room temperature under a nitrogen atmosphere. Then, 100 ml of 1 N hydrochloric acid was gradually added, and subsequently 100 ml of diethyl ether was added. The two-layered solution thus obtained was transferred to a 300-ml separatory funnel and the funnel was shaken several times. The aqueous layer was then removed. Subsequently, the organic layer obtained was washed 2 times with 100 ml of water and once with 100 ml of saturated brine, and dried over anhydrous magnesium sulfate for 3 hours. The solids were separated by filtration, and the solvent was distilled off. The residue was purified by separation using silica gel chromatography to obtain a target product (yield 1.28 g (51%)). The target product was identified by 1H-NMR and FD-MS spectroscopy.

1. customA 200-ml two-necked flask equipped with a magnetic stirrer
2. customwas thoroughly purged with nitrogen
3. temperaturewhile cooling the mixture in an ice water bath
4. additionwas gradually added over 30 minutes
5. temperaturewhile cooling the mixture in a methanol/dry ice bath
6. temperatureThe mixture was gradually warmed to room temperature
7. stirringstirred for 20 hours at room temperature under a nitrogen atmosphere
8. customThe two-layered solution thus obtained
9. customwas transferred to a 300-ml separatory funnel
10. stirringthe funnel was shaken several times
11. customThe aqueous layer was then removed
12. customSubsequently, the organic layer obtained
13. washwas washed 2 times with 100 ml of water
14. dry with materialonce with 100 ml of saturated brine, and dried over anhydrous magnesium sulfate for 3 hours
15. customThe solids were separated by filtration
16. distillationthe solvent was distilled off
17. customThe residue was purified by separation
18. customto obtain a target product (yield 1.28 g (51%))