反应详情

温度

-20 °C

100 ml of ether were placed in a round-bottomed flask containing 6.76 a (0.052 moles) of 2-methylindene (compound 1); the solution was cooled to −20° C. 21 ml of a 2.5 molar solution of butyllithium in hexane (0.052 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 hour. After cooling of the reaction mixture to −20° C., 5.0 g (0.052 moles) of chlorodimethylphosphine were added over 5 min to form a precipitate. The cooling bath was then removed and the reaction mixture was stirred for 1 h at room temperature. After cooling to −20° C., 21.0 ml of a 2.5 molar solution of butyllithium in hexane (0.052 moles) were added dropwise. When the addition was complete, the cooling bath was removed, after which the solution was heated slowly to room temperature and stirred for 1.5 h. After cooling of the suspension to 0° C., 16.9 g (0.052 moles) of chlorotributyltin were added dropwise. The suspension formed was heated to room temperature and stirred for 1.5 h. After removal of the ether 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 24.3 g (yield: 98%) of compound 19 in the form of a heavy yellow oil. 31P NMR (161.9 MHz, CDCl2): δ=−68.5 (s).

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