ammonia; sodium in tetrahydrofuran T=-50°C;

1.1: sodium hydride / mineral oil; ethylene glycol dimethyl ether / 1 h / 20 °C / |Inert atmosphere 1.2: 2 h / -15 - 20 °C / |Inert atmosphere 2.1: trimethylsilyl trifluoromethanesulfonate; triethylamine / dichloromethane / 6 h / 20 °C 3.1: dichloromethane / 0.25 h / 20 °C 3.2: 20 °C 4.1: 20 palladium(II) hydroxide on carbon; hydrogen / tetrahydrofuran; methanol / 67 h / 20 °C / 3750.38 Torr 5.1: lithium hydroxide hydrate; water / acetonitrile / 20 °C 6.1: lithium hydroxide hydrate / 1,4-dioxane / 24 h / pH 9 7.1: sodium; ammonia / tetrahydrofuran / 1 h / -70 - -50 °C View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 1.2: 1 h 1.3: 1 h 2.1: sodium hydride / mineral oil; ethylene glycol dimethyl ether / 1 h / 20 °C / |Inert atmosphere 2.2: 2 h / -15 - 20 °C / |Inert atmosphere 3.1: trimethylsilyl trifluoromethanesulfonate; triethylamine / dichloromethane / 6 h / 20 °C 4.1: dichloromethane / 0.25 h / 20 °C 4.2: 20 °C 5.1: 20 palladium(II) hydroxide on carbon; hydrogen / tetrahydrofuran; methanol / 67 h / 20 °C / 3750.38 Torr 6.1: lithium hydroxide hydrate; water / acetonitrile / 20 °C 7.1: lithium hydroxide hydrate / 1,4-dioxane / 24 h / pH 9 8.1: sodium; ammonia / tetrahydrofuran / 1 h / -70 - -50 °C View Scheme