1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / |Inert atmosphere 1.2: 1 h / 0 - 20 °C / |Inert atmosphere 2.1: tetrahydrofuran; mineral oil / 5 h / 0 - 20 °C / |Inert atmosphere 3.1: tetrahydrofuran; mineral oil / |Reflux; |Inert atmosphere 4.1: tetrabutylammomium bromide; potassium permanganate; acetic acid / dichloromethane; water / 36 h / |Reflux 5.1: borane dimethyl sulfide complex / tetrahydrofuran / 12 h / 0 - 20 °C / |Inert atmosphere 5.2: 0.5 h / 0 °C View Scheme

potassium permanganate; tetrabutylammomium bromide; acetic acid in dichloromethane; water 24 h; Reflux;

1: 1-bromo-3-methyl-butane With iodine; magnesium in tetrahydrofuran 2 h; Heating / reflux; 2: 12-hydroxydodecyl bromide With dilithium tetrachlorocuprate in tetrahydrofuran T=-78 - 20°C;

1: 1-bromo-3-methyl-butane With magnesium in tetrahydrofuran 2: 12-hydroxydodecyl bromide With dilithium tetrachlorocuprate in tetrahydrofuran T=-78 - 20°C;

1: 95 percent / 3 h / 120 °C 2: 1.) BuLi / 1.) THF, 0 deg C, 45 min, 2.) THF, RT, 2 h 3: H2 / 5 percent Pt/C / methanol / 6 h / 760 Torr / Ambient temperature View Scheme

palladium 10 on activated carbon; hydrogen in ethanol T=20°C; 12 h;

1,4-dioxane; copper (II) chromite T=250°C; P=102236 Torr; Hydrogenation;

lithium aluminium tetrahydride; diethyl ether

1: toluene; sulfuric acid / Entfernen des enstehenden Wassers 2: lithium alanate; diethyl ether View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / |Inert atmosphere 1.2: 1 h / 0 - 20 °C / |Inert atmosphere 2.1: tetrahydrofuran; mineral oil / 5 h / 0 - 20 °C / |Inert atmosphere 3.1: tetrahydrofuran; mineral oil / |Reflux; |Inert atmosphere 4.1: tetrabutylammomium bromide; potassium permanganate; acetic acid / dichloromethane; water / 36 h / |Reflux 5.1: borane dimethyl sulfide complex / tetrahydrofuran / 12 h / 0 - 20 °C / |Inert atmosphere 5.2: 0.5 h / 0 °C 6.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / |Inert atmosphere 6.2: 1 h / 0 - 20 °C / |Inert atmosphere 7.1: tetrahydrofuran; mineral oil / 5 h / 0 - 20 °C / |Inert atmosphere 8.1: tetrahydrofuran; mineral oil / |Reflux; |Inert atmosphere 9.1: tetrabutylammomium bromide; potassium permanganate; acetic acid / dichloromethane; water / 36 h / |Reflux View Scheme