1.1: BuLi / hexane; tetrahydrofuran / 1 h / -50 - 20 °C 1.2: 71 percent / hexane; tetrahydrofuran / 5.25 h 2.1: t-BuLi / tetrahydrofuran; pentane / 0.05 h / -110 - -40 °C 2.2: H2O / tetrahydrofuran; pentane / 20 °C 2.3: tetrahydrofuran; pentane / 3 h / 67 °C 3.1: 0.19 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C View Scheme

1.1: BuLi / hexane; tetrahydrofuran / 1 h / -50 - 20 °C 1.2: 71 percent / hexane; tetrahydrofuran / 5.25 h 2.1: t-BuLi / tetrahydrofuran; pentane / -110 - 20 °C 2.2: BrCH2CH2Br / tetrahydrofuran; pentane / -78 - 20 °C 3.1: 0.21 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C View Scheme

1.1: BuLi / tetrahydrofuran / -50 - 20 °C 1.2: 78 percent / tetrahydrofuran / 0.25 h / -50 °C 2.1: tBuLi / tetrahydrofuran / -110 - 20 °C 2.2: MeOH / tetrahydrofuran / -78 - 20 °C 3.1: DIBAL-H; [NiCl2(dppp)] / toluene / 2 h / 20 °C 4.1: 0.214 g / PCC / CH2Cl2 / 2 h / Heating View Scheme

1.1: BuLi / hexane; tetrahydrofuran / 1 h / -50 - 20 °C 1.2: 74 percent / hexane; tetrahydrofuran / 5.25 h 2.1: t-BuLi / tetrahydrofuran; pentane / -110 - 20 °C 2.2: 71 percent / H2O / tetrahydrofuran; pentane / 3 h / 20 °C 3.1: 0.25 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C View Scheme