1.1: p-toluenesulfonic acid monohydrate / benzene / 12 h / |Dean-Stark; |Reflux; |Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / |Inert atmosphere 3.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / |Inert atmosphere 3.2: 1 h / 0 - 20 °C / |Inert atmosphere 4.1: triphenylphosphine; iodine; 1H-imidazole / benzene; diethyl ether / 12 h / 20 °C / |Inert atmosphere 5.1: tert.-butyl lithium / diethyl ether; pentane / 1 h / -78 °C / |Inert atmosphere 5.2: 0.5 h / -78 °C / |Inert atmosphere 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / |Inert atmosphere 7.1: dipyridinium dichromate / dichloromethane / 12 h / 20 °C / |Reflux; |Inert atmosphere 8.1: samarium diiodide / tetrahydrofuran; tert-butyl alcohol / 12 h / 0 °C / |Inert atmosphere 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / 0 - 20 °C / |Inert atmosphere 10.1: Amberlyst-15 / benzene / 12 h / 20 °C / |Reflux View Scheme

1.1: ethylamine / ethanol / 48 h / 20 °C 1.2: 0.17 h / 100 °C 2.1: trichlorophosphate / 24 h / 180 °C 3.1: potassium acetate; hydrogen; palladium on activated charcoal / methanol / 24 h / 20 °C 4.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 0 - 20 °C 5.1: acetic acid; hydrogen; palladium(II) oxide hydrate / 80 °C View Scheme

hydrazine in ethanol T=20 - 80°C; 3 h;

Erhitzen;

Unter Abdestillieren des gebildeten Aethanols.;

sodium acetate in methanol T=32°C; 15 h;

hydroxylamine hydrochloride in methanol; water 6 h; Ambient temperature;

toluene-4-sulfonic acid in chloroform 6 h; Heating / reflux;

sodium ethanolate; acetic acid 1.) EtOH, reflux, 7 h; 2.) acetone; Yield given. Multistep reaction;

1.1: Ac2O / 1 h / 135 °C 1.2: 54 percent / H2O / 16 h / 20 °C 2.1: POCl3; Et3N / 16 h 3.1: [1-chloromethyl-4-F-1,4-diazoniabicyclo[2.2.2]octane]*(BF4)2 / acetonitrile / 1 h / 85 °C View Scheme