Indene → Tributylstannyldimethylphosphinoindene

関与物質

反応条件

反応手順

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.

情報源と証拠