Tetrahydrofuran → [2-(tri-n-Butylstannyl)-1-ethynyl]cyclobutane

Participants

Reaction Steps

To a solution of n-BuLi/hexane (7.28 mL, 18.2 mmol, 2.5 M) at −5° C. was added tetrahydrofuran dropwise, maintaining the temperature below +9° C. 6-Chloro-1-hexyne (1.00 mL, 8.92 mmol) was added at +5° C., and the solution was stirred for six hours. The reaction was quenched by the addition of tri-n-butyltin chloride (2.66 mL, 9.81 mmol), and was allowed to stir for an additional 10 minutes. The solution was poured into hexane, washed with saturated NaHCO3 solution and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was isolated as a colorless liquid which was used without further purification.

Provenance & Evidence