反应详情

温度

22 °C

10.6 millimoles of n-butyllithium as a 0.53 Normal solution in benzene was admixed with 4.06 grams of methyltriphenylphosphonium bromide dissolved in 50 milliliters of tetrahydrofuran in a nitrogen-purged glass reaction vessel and the vessel maintained at ambient temperature (about 22° C.) for a period of 2 hours. A suspension of 2.05 grams of Compound VI in 30 milliliters of tetrahydrofuran was added to the reaction mixture. The reaction vessel was maintained at room temperature for a period of about 16 hours. At the end of this period, the tetrahydrofuran was evaporated and the remaining solid dissolved in a 1:1 by volume diethyl ether-water mixture. The ether and water were separated and the ether layer washed with water and subsequently the ether was evaporated. The crude product Compound VII was recrystallized twice from a 1 to 1 mixture of benzene and ethanol and the solid product obtained washed with n-hexane, the 4,4'-bis(1-phenylethenyl)-1,1'-biphenyl (Compound VII) had a melting point of 193°-196° C. A benzene solution of Compound VII was prepared in a nitrogen-filled serum bottle equipped with a magnetic stirrer. The solution contained 0.5 grams (1.41 millimoles) of Compound VII and 70 milliliters of dry benzene. 7.2 milliliters of 0.482 Normal secondary butyllithium n-hexane solution was injected into the serum bottle with a hypodermic syringe to provide 3.47 milliequivalents of sec-butyllithium. The mixture was stirred at room temperature for 2 hours and 40 minutes, and resulted in a deep blue colored dispersion.

1. custompurged
2. customglass reaction vessel
3. additionwas added to the reaction mixture
4. temperatureThe reaction vessel was maintained at room temperature for a period of about 16 hours
5. customAt the end of this period, the tetrahydrofuran was evaporated
6. dissolutionthe remaining solid dissolved in a 1:1 by volume diethyl ether-water mixture
7. customThe ether and water were separated
8. washthe ether layer washed with water
9. customsubsequently the ether was evaporated
10. customThe crude product Compound VII was recrystallized twice from a 1 to 1 mixture of benzene and ethanol
11. customthe solid product obtained
12. washwashed with n-hexane
13. additionfilled serum bottle
14. customequipped with a magnetic stirrer