1.1: 86 percent / kerosene / 1 h / Heating 2.1: 67 percent / tin(II) chloride; acetic acid; hydrochloric acid / 24 h / Heating 3.1: sodium nitrite; aq. HCl / 2 h / 0 °C 3.2: potassium iodide / H2O / 24 h / 20 °C 4.1: 1.57 g / NaOH / benzyltrimethylammonium chloride / dimethylsulfoxide; H2O / 3 h / 80 °C 5.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C 5.2: 42.4 percent / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1: 86 percent / kerosene / 1 h / Heating 2: 67 percent / tin(II) chloride; acetic acid; hydrochloric acid / 24 h / Heating View Scheme