tetra-(n-butyl)ammonium iodide; potassium carbonate in N,N-dimethyl-formamide T=20°C; 14 h; Inert atmosphere;

1.1: lithium diisopropyl amide / tetrahydrofuran / 1.25 h / -78 - 20 °C / |Inert atmosphere 1.2: 14 h / 0 °C / |Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 14 h / 20 °C / |Inert atmosphere View Scheme

1.1: 77 percent / ethanol / 20 h / 20 °C 2.1: tert-BuLi / diethyl ether; pentane / 6.5 h / 20 °C 2.2: BrCCl2CCl2Br / diethyl ether; pentane / 12 h / 20 °C 3.1: 815 mg / aq. HCl / diethyl ether; pentane / 0.5 h / 20 °C 4.1: 565 mg / KOH / ethanol / 5 h / Heating View Scheme

1.1: tert-BuLi / diethyl ether; pentane / 6.5 h / 20 °C 1.2: BrCCl2CCl2Br / diethyl ether; pentane / 12 h / 20 °C 2.1: 815 mg / aq. HCl / diethyl ether; pentane / 0.5 h / 20 °C 3.1: 565 mg / KOH / ethanol / 5 h / Heating View Scheme

potassium hydroxide in ethanol Etherification; 5 h; Heating;