Indene → HCID 70151496, compound

Participants

Reaction Conditions

Reaction Steps

100 ml of ether were placed in a round-bottomed flask containing 3.8 g (0.033 moles) of indene and the solution was cooled to −20° C. 14.4 ml of a 2.3 molar solution of butyllithium in hexane (0.033 moles) were added over 5 minutes to form a yellow solution. After removal of the cooling bath, the solution was heated to room temperature and subsequently stirred for 1.5 h. The reaction mixture was then cooled to 0° C. and 5.0 g of chlorodiisopropylphosphine (0.033 moles) were added to form a precipitate. After removal of the cooling bath, the solution was heated to room temperature and stirred for 1 h. The solution was then cooled to −20° C. and 14.4 ml of a 2.3 molar solution of butyllithium in hexane (0.033 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., 10.1 g of chlorotributyltin (0.031 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 16.6 g of compound 8 (yield: 97%) in the form of a heavy yellow oil. Two isomers were obtained in proportions of 1.5:1. The main isomer was identified as follows: 1H NMR (400 MHz, CD2Cl2): δ=7.71 (d, J=7.2 Hz, 1H); 7.41 (d, J=7.3 Hz, 1H); 7.13 (m, 2H); 6.96 (m, 1H); 4.28 (s with Sn satellites, 1H); 2.21 (m, 1H); 1.54 (m, 1H); 1.45-0.65 (m, 39H); 31P NMR (161.9 MHz, CD2Cl2): δ=−11.3 ppm. The secondary isomer was identified as follows: 1H NMR (400 MHz, CD2Cl2): δ=7.6 (d, J=7.4 Hz, 1H); 7.46 (d, J=7.2 Hz, 1H); 7.26 (t, J=7.5 Hz, 1H); 7.1 (m, 1H); 6.71 (m, 1H); 3.48 (m, 1H); 2.21 (m, 1H); 1.54 (m, 1H); 1.45-0.65 (m, 39H); 31P NMR (161.9 MHz, CD2Cl2): d=−1.5 ppm.

Provenance & Evidence