Trimethyltin chloride → HCID 58517355, compound

Participants

Reaction Conditions

Reaction Steps

(E)-1,2-Bis(3-dodecylthienyl)ethylene (12) (10.4 mmol, 2.00 g) was dissolved in anhydrous THF (43.2 mL) and cooled to −78° C. under nitrogen. n-Butyllithium (21.84 mmol, 13.7 mL) was then added dropwise. The resulting solution was warmed to room temperature over 30 min and stirred at that temperature for 3 h. The mixture was then cooled to −78° C. before trimethyltin chloride (21.84 mmol, 4.35 g) in anhydrous THF (26 mL) was added dropwise. After addition, the mixture was warmed to room temperature over 4 h and stirred for additional 20 h at room temperature. The reaction mixture was poured into saturated NH4Cl solution (100 mL) and the aqueous layer was extracted with diethyl ether. The combined organic layers were washed with water, dried over Na2SO4 and concentrated under reduced pressure. The crude solid was recrystallized from ethanol to give desired product 13 in 73% yield. 1H-NMR (CDCl3, 400 MHz) ppm 0.36 (s, 18H) ppm 0.88 (t, 6H, J=6.9 Hz) ppm 1.30 (m, 36H) ppm 1.59 (td, 4H, J=7.3 Hz, J=14.9 Hz) ppm 2.65 (m, 4H) ppm 6.94 (s, 2H) ppm 7.00 (s, 2H).

Provenance & Evidence