反应详情

温度

-20 °C

150 ml of ether were placed in a round-bottomed flask containing 5.5 g (0. 047 moles) of indene; the solution was cooled to −20° C. 20.8 ml of a 2.3 molar solution of butyllithium in hexane (0.048 moles) were added over 5 min to form a yellow solution. After removal of the cooling bath, the solution was heated to room temperature and subsequently stirred for 1 h. After cooling of the reaction mixture to −30° C., 4.6 g of chlorodimethylphosphine (0.048 moles) in 30 ml of ether were added over 20 min to form a precipitate. After stirring for 2 hours at −20° C., 20.8 ml of a 2.3 molar solution of butyllithium in hexane (0.048 moles) were added dropwise. When the addition was complete, the cooling bath was removed and the solution was heated slowly to room temperature and stirred for 1.5 h. After cooling of the suspension to 0° C., 15.6 g of chlorotributyltin (0.048 moles) were added dropwise. The suspension formed was heated to room temperature and stirred for 1.5 h. The ether was removed under vacuum, the crude product was dissolved in hexane again, the solution was filtered and the filtrate was concentrated to dryness under vacuum to leave 17.4 g of compound 10 (yield: 78%) in the form of a heavy yellow oil. 1H NMR (400 MHz, CD2Cl2): δ=7.67 (d, J=7.5 Hz, 1H); 7.47 (d, J=7.4 Hz, 1H); 7.18 (m, 2H); 6.83 (m, 1H); 4.28 (s with Sn satellites, 1H); 1.43-0.78 (m, 33H); 3P NMR (161.9 MHz, CD2Cl2): δ=−61.6 ppm.

1. customto form a yellow solution
2. customAfter removal of the cooling bath
3. temperaturethe solution was heated to room temperature
4. temperatureAfter cooling of the reaction mixture to −30° C.
5. customto form a precipitate
6. stirringAfter stirring for 2 hours at −20° C.
7. additionWhen the addition
8. customthe cooling bath was removed
9. temperaturethe solution was heated slowly to room temperature
10. stirringstirred for 1.5 h
11. temperatureAfter cooling of the suspension to 0° C.
12. customThe suspension formed
13. temperaturewas heated to room temperature
14. stirringstirred for 1.5 h
15. customThe ether was removed under vacuum
16. dissolutionthe crude product was dissolved in hexane again
17. filtrationthe solution was filtered
18. concentrationthe filtrate was concentrated to dryness under vacuum