Hexane → HCID 70150555, compound

Participants

Reaction Conditions

Reaction Steps

100 ml of ether were placed in a round-bottomed flask containing 5.0 g (0.035 moles) of 4,7-dimethylindene (compound 21); the solution was cooled to −20° C. 14 ml of a 2.5 molar solution of butyllithium in hexane (0.035 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 −20° C., 5.3 g (0.035 moles) of chlorodiisopropylphosphine 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., 14.0 ml of a 2.5 molar solution of butyllithium in hexane (0.035 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., 11.4 g of chlorotributyltin (0.035 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 under vacuum to leave 16 g (yield: 83%) of compound 22 in the form of a heavy yellow oil. 31P NMR (161.9 MHz, CD2Cl2): δ=−9 ppm.

Provenance & Evidence