1.1: BuLi / hexane; tetrahydrofuran / 1.25 h / -50 - 20 °C 1.2: 75 percent / hexane; tetrahydrofuran / 5.25 h 2.1: BuLi / hexane; tetrahydrofuran / 1 h / -50 - 20 °C 2.2: 74 percent / hexane; tetrahydrofuran / 5.25 h 3.1: t-BuLi / tetrahydrofuran; pentane / -110 - 20 °C 3.2: 71 percent / H2O / tetrahydrofuran; pentane / 3 h / 20 °C 4.1: 0.25 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C View Scheme

1: sodium nitrite; hydrogenchloride / water / 10 °C 2: silver(I) acetate; [{(η5-C5Me5)RhCl}2(μ-Cl)2]; silver hexafluoroantimonate / methanol / 8 h / 35 °C 3: hydrogen / methanol / 3 h / 20 °C / |Schlenk technique View Scheme

1.1: BuLi / tetrahydrofuran / -50 - 20 °C 1.2: 77 percent / tetrahydrofuran / 0.25 h / -50 °C 2.1: tBuLi / tetrahydrofuran / -110 - 20 °C 2.2: 42 percent / MeOH / tetrahydrofuran / -78 - 20 °C 3.1: 0.329 g / air / 250 °C View Scheme