1.1: sodium tetrahydroborate / methanol / 2 h / 20 °C 2.1: sodium hydride / dichloromethane / 0.33 h 2.2: 2 h 3.1: copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere View Scheme

diethylzinc in hexane; toluene T=20°C; 5 h;

1: 92 percent / 2.5M BuLi / hexane; tetrahydrofuran / 4 h / -78 °C 2: 58 percent / NaOH / ethanol / 12 h / 90 °C View Scheme