In a flame-dried 250 mL flask, LHMDS (97%, 3.28 g, 19.6 mmol) and LiCl (1.72 g, 40.5 mmol) were added. The flask was sealed and placed under N2 on the bench. THF (10 mL) was added at 22 °C, and the thin slurry was cooled to –78 °C. In a 100 mL flask containing amide 11 (3.00 g, 9.45 mmol), THF (60 mL) was charged, and the solution was cannula transferred to the LHMDS/LiCl solution at –78 °C. The light copper colored solution was warmed to 22 °C, and kept at this temperature for 30 minutes. The reaction was cooled to –78 °C, and bromide 10 (1.71g, 6.75 mmol) in THF (20 mL) was cannula transferred to the amide enolate with a 10 mL THF wash. After 10 minutes, TLC was used to assess completion of reaction. Solution was quenched with aqueous saturated NH4Cl and extracted three times with EtOAc. The combined organic layers were dried over Na2SO4, concentrated in vacuo, and purified by silica gel S11 chromatography (0 → 40% EtOAc/hexanes) to provide 3.29 g (90% yield) light yellow oil, triyne 12.