Trimethyltin chloride → HCID 58434863, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2.9 g (5.42 mmol) of 3,3′-didodecyloxy-2,2′-bithiophene (Org. Lett. 2008, 10, 5333) in 150 mL of THF was cooled to −78° C. The resulting suspension was treated dropwise with 5.2 mL (13.0 mmol) of n-BuLi (2.5 M in hexanes) and stirred for an additional 45 minutes. The dry ice bath was then removed and the mixture was stirred at ambient temperature for 1.25 hours. The suspension was cooled to −78° C. and treated with a solution of 3.02 g (15.2 mmol) of trimethyltin chloride in 15 mL of THF. The mixture was stirred for 90 minutes at ambient temperature. The mixture was diluted with 100 mL of ethyl acetate and washed successively with 50 mL of water and 50 mL of brine. The separated organic layer was dried over K2CO3, filtered, and concentrated in vacuo. The resulting solid was recrystallized from cold pentane to give 3.8 g (81% yield) of 5,5′-bis(trimethylstannyl)-3,3′-bis(dodecyloxy)2,2′-bithiophene as light tan needles. m.p. 66-67° C. 1H NMR (500 MHz) δ 6.88 (s, 2H), 4.11 (t, 4H, J=6.4 Hz), 1.84 (m, 4H), 1.55-1.30 (m, 36H), 0.88 (m, 6H), 0.36 (s, 18H).

Provenance & Evidence