Tributylstannane → (E)-triethoxy(2-(tributylstannyl)vinyl)silane

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Tributyltin hydride (1.9 mL, 7.2 mmol, 1.0 equiv) and triethoxy(ethynyl)silane (1.5 g, 7.9 mmol, 1.1 equiv) were combined. AIBN (60 mg, 0.36 mmol, 0.05 equiv) was added and the resulting yellow solution was heated to 80° C. Upon reaching 80° C., the reaction exothermed to 104° C. The yellow solution was cooled back to 80° C. and stirred for 20 h. The reaction mixture was cooled to provide the title compound as a pale yellow oil (3.5 g, 99% crude yield): IR (thin film) 2957 (s), 2925 (s), 2873 (m), 2854 (m) cm−1; 1H NMR (400 MHz, CDCl3) δ 7.43 (d, J=24 Hz, 1H), 6.37 (d, J=24 Hz, 1H), 3.83 (q, J=7 Hz, 6H), 1.49 (m, 6H), 1.29 (m, 6H), 1.22 (t, J=7 Hz, 9 H), 0.82-0.92 (m, 15 H).

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