sulfuric acid

1: neat (no solvent) / 100 °C 2: 24.3 g / Br2, PCl3 / 1.) 80 - 85 deg C, 3 h, 2.) 100 deg C, 1 h View Scheme

1: 2-Carboxy-4-methylpentanoic acid With diethylamine in ethyl acetate T=0 - 23°C; RefluxInert atmosphere; 2: formaldehyd in ethyl acetate 5 h; RefluxInert atmosphere;

chloroform; tris-(2-chloro-ethyl)-amine; sulfuric acid

1.1: diethylamine / ethyl acetate / Reflux 1.2: Reflux 2.1: sulfuric acid / 12 h / Reflux 3.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / diethyl ether / 2 h / -20 - 20 °C 4.1: triethylamine / dichloromethane / 3 h / 0 °C 5.1: sodium azide / dimethyl sulfoxide / 20 h / 70 °C / Inert atmosphere 6.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 6.2: 20 h / 20 °C 7.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 8.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 9.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 10.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 11.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C View Scheme

durch Destillation;

1.1: diethylamine / ethyl acetate / Reflux 1.2: Reflux 2.1: sulfuric acid / 12 h / Reflux 3.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / diethyl ether / 2 h / -20 - 20 °C 4.1: triethylamine / dichloromethane / 3 h / 0 °C 5.1: sodium azide / dimethyl sulfoxide / 20 h / 70 °C / Inert atmosphere 6.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 6.2: 20 h / 20 °C 7.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 8.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 9.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 10.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 11.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 12.1: hydrogenchloride / water / 24 h / Reflux 12.2: pH 4 - 5 View Scheme

1.1: diethylamine / ethyl acetate / Reflux 1.2: Reflux 2.1: sulfuric acid / 12 h / Reflux 3.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / diethyl ether / 2 h / -20 - 20 °C 4.1: triethylamine / dichloromethane / 3 h / 0 °C 5.1: sodium azide / dimethyl sulfoxide / 20 h / 70 °C / Inert atmosphere 6.1: triphenylphosphine / diethyl ether / 1 h / 0 °C 6.2: 20 h / 20 °C 7.1: potassium carbonate / dichloromethane / 4.42 h / 0 - 20 °C 8.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 5 h 9.1: Grubb's 2nd generation catalyst / toluene / 15 h / 80 °C / Inert atmosphere 10.1: sodium tetrahydroborate; NiII chloride hexahydrate / methanol / 1.25 h / 15 °C 11.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C 12.1: hydrogenchloride / water / 24 h / Reflux 12.2: pH 4 - 5 View Scheme

sodium hydroxide in ethanol; water T=23°C; 21 h; Inert atmosphere;

sodium ethanolate in ethanol