反应详情

温度

0 °C

In a nitrogen atmosphere, N-iodosuccinimide (1.1 g, 5.0 mmol) was added to an acetonitrile solution of (Z)-(1-(4-methoxyphenyl)-2-(5-methyl-2-thienyl)-ethenyl)trimethylsilane (0.3 g, 1.0 mmol) at 0° C. The mixture was stirred for 5 hours while maintaining at 0° C., and then applied to an alumina column for concentration. In a nitrogen atmosphere, the residue obtained was dissolved in diethyl ether, and n-butyl lithium (0.9 mL, 1.4 mmol) was added dropwise at −78° C. The mixture was stirred for 1 hour while maintaining at −78° C., and dimesityl boron fluoride (0.37 g, 1.56 mmol) was then added thereto. The mixture was stirred at room temperature for 12 hours, and water was then added thereto, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution and then dried with magnesium sulfate, followed by filtration. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane) and recrystallization (diethyl ether). Thus, (E)-(1-(4-methoxyphenyl)-2-(5-methyl-2-thienyl)ethenyl)-bis(2,4,6-trimethylphenyl)borane was obtained.

1. concentrationapplied to an alumina column for concentration
2. customIn a nitrogen atmosphere, the residue obtained
3. stirringThe mixture was stirred for 1 hour
4. temperaturewhile maintaining at −78° C.
5. stirringThe mixture was stirred at room temperature for 12 hours
6. extractionfollowed by extraction with ethyl acetate
7. washThe organic layer was washed with a saturated sodium chloride solution
8. dry with materialdried with magnesium sulfate
9. filtrationfollowed by filtration
10. concentrationThe filtrate was concentrated
11. customthe residue was purified by silica gel column chromatography (dichloromethane) and recrystallization (diethyl ether)