反应详情

温度

-78 °C

Under a nitrogen atmosphere, 30 mL of dehydrated tetrahydrofuran was added to 1.51 g (3.51 mmol) of 2,7-diphenyl-3,6-ditert-butyl-fluorene synthesized in Synthesis Example 1-1 (ii), and the mixture was stirred. This solution was cooled in an ice bath, and 2.50 mL (3.90 mmol) of a 1.56 mol/L hexane solution of n-butyllithium was added. The mixture was stirred at room temperature for 2 hours. The resulting dark red solution was cooled to −78° C. in a dry ice/methanol bath, and a tetrahydrofuran solution prepared by dissolving 0.757 g (3.98 mmol) of 6,6-di(n-butyl)fulvene in 15 mL of tetrahydrofuran was added dropwise over 15 minutes. Subsequently, the mixture was stirred for 18 hours while gradually warming to room temperature. 50 mL of 1 N hydrochloric acid was added to the resulting red solution to terminate the reaction. 100 mL of diethyl ether was added to perform liquid-liquid phase separation, and the soluble fraction was extracted. This organic layer was washed two times with a saturated aqueous solution of sodium hydrogen carbonate, two times with water and once with saturated brine, and dried over magnesium sulfate. The solvent was distilled off, and the residue was recrystallized from hexane to obtain a target product as a white powder (yield 1.54 g (70%)). The target product was identified by 1H-NMR and FD-MS spectroscopy.

1. temperatureThis solution was cooled in an ice bath
2. stirringThe mixture was stirred at room temperature for 2 hours
3. additionwas added dropwise over 15 minutes
4. stirringSubsequently, the mixture was stirred for 18 hours
5. temperaturewhile gradually warming to room temperature
6. customto terminate
7. customthe reaction
8. customliquid-liquid phase separation
9. extractionthe soluble fraction was extracted
10. washThis organic layer was washed two times with a saturated aqueous solution of sodium hydrogen carbonate, two times with water
11. dry with materialonce with saturated brine, and dried over magnesium sulfate
12. distillationThe solvent was distilled off
13. customthe residue was recrystallized from hexane