toluene-4-sulfonic acid in toluene 5 h; Heating;

lithium aluminium tetrahydride in tetrahydrofuran 0.5 h; Heating;

sodium tetrahydroborate in ethanol 3 h; Heating;

samarium diiodide in tetrahydrofuran T=20°C; 0.333333 h;

samarium diiodide in tetrahydrofuran T=20°C;

1.1: 88 percent / methanol / 20 °C 2.1: 66 percent / 120 °C / 0.5 Torr 3.1: NaHMDS / tetrahydrofuran / -78 - 20 °C 3.2: SiO2 4.1: 82 percent / aq. HCl / dioxane / 0.67 h / 50 °C 5.1: 95 percent / pyridine; DMAP / CH2Cl2 / 1 h / 20 °C 6.1: NaIO4; RuCl3 / acetonitrile; CCl4; H2O / 6 h 7.1: 36 mg / diethyl ether; methanol; hexane / 0.5 h / 20 °C 8.1: 92 percent / NaOMe / methanol / 1 h / 20 °C View Scheme

in methanol T=20°C;

sodium methylate Ambient temperature;

sodium in ethanol Ambient temperature;

sodium tetrahydroborate in ethanol 3 h; Heating;