Reaction Steps
A 250-mL round-bottom flask equipped with a stir bar and a water-jacketed reflux condenser was charged with trimethylsilylacetylene (6.00 mL, 42.0 mmol). THF (50 mL) was added, and the mixture was allowed to cool to 0° C. (ice-bath). nButyllithium (29.0 mL, 42.0 mmol, 1.46 M solution in hexanes) was added dropwise by a syringe, and the ice-bath was removed following the addition. The mixture was allowed to warm to 22° C. as it stirred for 1 h, at which point 8-bromo-1-octene (3.50 mL, 21.0 mmol) was added, and the mixture was allowed to reflux for 12 h. The mixture was allowed to cool to 0° C., quenched by addition of 50 mL water, washed with CH2Cl2 (5×50 mL). The combined organic layers were washed in brine (1×50 mL), dried over MgSO4, filtered, and concentrated in vacuo. The resulting brown oil was filtered through a plug of silica gel (eluted in pentane), the filtrate was concentrated and the resulting brown oil distilled under vacuum (1.0 torr). The resulting yellow oil was re-distilled under vacuum (1.0 ton) to afford dec-9-en-1-ynyltrimethylsilane (0.700 g, 3.40 mmol, 14.0% yield) as a colorless oil. IR (neat): 3078 (w), 2929 (m), 2857 (w), 2175 (m), 1641 (w), 1461 (w), 1325 (w), 1248 (m), 1032 (w), 994 (w), 910 (m), 837 (s), 758 (s), 725 (w), 697 (w), 638 (m), 575 (w), 450 (w); 1H NMR (400 MHz, CDCl3): δ 5.86-5.76 (1H, m), 4.99 (1H, dd, J=17.2, 2.0 Hz), 4.93 (1H, dd, J=10.0,0.8 Hz), 2.21 (2H, t, J. 7.2 Hz), 2.05 (2H, app q, J=7.1 Hz), 1.55-1.48 (2H, m), 1.40-1.28 (6H, m), 0.14 (9H, s); 13C NMR (100 MHz, CDCl3): δ 139.2, 114.4, 107.8, 84.4, 33.9, 28.9, 28.8, 28.7, 28.7, 20.0, 0.3; HRMS (ESI+) [M+H]+ calcd for C13H25Si: 209.1726, found: 209.1719.
