1.1: tBuLi / tetrahydrofuran / -110 - 20 °C 1.2: 1,2-dibromoethane / tetrahydrofuran / -78 - 20 °C 2.1: DIBAL-H; [NiCl2(dppp)] / toluene / 2 h / 20 °C 2.2: 0.395 g / PCC / CH2Cl2 / 2 h / Heating View Scheme

1.1: t-BuLi / tetrahydrofuran; pentane / -110 - 20 °C 1.2: 71 percent / H2O / tetrahydrofuran; pentane / 3 h / 20 °C 2.1: 0.25 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C View Scheme