反应详情

温度

1 °C

In a 200 ml three-necked flask purged with nitrogen, 2.64 g (6.83 mmol, 1 eq) of 1,1,4,4,7,7,10,10-octamethyl-1,2,3,4,7,8,9,10-octahydrodibenzo(b,h)-fluorene was placed at room temperature. Then, 40 ml of dehydrated THE was added, and the mixture was stirred by a magnetic stirrer to give a solution. The solution was cooled with an ice bath (light yellow solution). To the solution, 4.6 ml (7.50 mmol, 1.10 eq) of a hexane solution of n-BuLi was dropwise added over a period of 10 minutes. Then, the ice bath was removed, and the solution was stirred at room temperature for 23 hours (dark red solution). The solution was cooled to 1° C. with an ice bath, and to the solution, a solution of 2.06 (8.94 mmol, 1.31 eq) of 6,6-diphenylfulvene in 20 ml of dehydrated THF was dropwise added over a period of 20 minutes (dark red slurry). The ice bath was removed, and the solution was stirred at room temperature for 65 hours. The resulting dark reddish brown solution was poured into 100 ml of a diluted hydrochloric acid solution to perform quenching. From the aqueous layer, the soluble component was extracted with diethyl ether, and the organic phase was washed with 100 ml of a saturated saline solution. The dispensed organic phase was dried over MgSO4, then the MgSO4 was filtered off, and from the filtrate the solvent was vacuum distilled off by a rotary evaporator to obtain an orangy yellow amorphous product. The amorphous product was washed with methanol, then filtered and dried in a vacuum disiccator to obtain 3.31 g of a slightly yellow powder (yield: 79%).

1. customwas placed at room temperature
2. additionThen, 40 ml of dehydrated THE was added
3. customto give a solution
4. temperatureThe solution was cooled with an ice bath (light yellow solution)
5. customThen, the ice bath was removed
6. stirringthe solution was stirred at room temperature for 23 hours (dark red solution)
7. customThe ice bath was removed
8. stirringthe solution was stirred at room temperature for 65 hours
9. additionThe resulting dark reddish brown solution was poured into 100 ml of a diluted hydrochloric acid solution
10. customto perform quenching
11. extractionFrom the aqueous layer, the soluble component was extracted with diethyl ether
12. washthe organic phase was washed with 100 ml of a saturated saline solution
13. dry with materialThe dispensed organic phase was dried over MgSO4
14. filtrationthe MgSO4 was filtered off
15. distillationdistilled off by a rotary evaporator
16. customto obtain an orangy yellow amorphous product
17. washThe amorphous product was washed with methanol
18. filtrationfiltered
19. customdried in a vacuum disiccator