sodium hydride in tetrahydrofuran; oil T=75°C; Inert atmosphereCooling with ice;

1.1: sodium hydroxide / ethanol / 4 h / Reflux 2.1: 130 - 140 °C / neat (no solvent) 3.1: thionyl chloride / 1 h / Reflux 4.1: 0.17 h / Reflux 5.1: sodium hydroxide 5.2: 20 h / Reflux 6.1: thionyl chloride 7.1: pyridine; 4-(N,N-dimethlyamino)pyridine / diethyl ether / 0.33 h 8.1: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / benzene / 25 °C / Cooling with liquid nitrogen; Sealed tube; UV-irradiation View Scheme

1.1: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / benzene / 25 °C / Cooling with liquid nitrogen; Sealed tube; UV-irradiation 2.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / Inert atmosphere 2.2: 0.75 h / Inert atmosphere 3.1: sodium hydroxide / ethanol / 4 h / Reflux 4.1: 130 - 140 °C / neat (no solvent) 5.1: thionyl chloride / 1 h / Reflux 6.1: 0.17 h / Reflux 7.1: sodium hydroxide 7.2: 20 h / Reflux 8.1: thionyl chloride 9.1: pyridine; 4-(N,N-dimethlyamino)pyridine / diethyl ether / 0.33 h 10.1: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / benzene / 25 °C / Cooling with liquid nitrogen; Sealed tube; UV-irradiation View Scheme

1.1: sodium hydroxide 1.2: 20 h / Reflux 2.1: thionyl chloride 3.1: pyridine; 4-(N,N-dimethlyamino)pyridine / diethyl ether / 0.33 h 4.1: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / benzene / 25 °C / Cooling with liquid nitrogen; Sealed tube; UV-irradiation View Scheme

1: thionyl chloride 2: pyridine; 4-(N,N-dimethlyamino)pyridine / diethyl ether / 0.33 h 3: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / benzene / 25 °C / Cooling with liquid nitrogen; Sealed tube; UV-irradiation View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / Inert atmosphere 1.2: 0.75 h / Inert atmosphere 2.1: sodium hydroxide / ethanol / 4 h / Reflux 3.1: 130 - 140 °C / neat (no solvent) 4.1: thionyl chloride / 1 h / Reflux 5.1: 0.17 h / Reflux 6.1: sodium hydroxide 6.2: 20 h / Reflux 7.1: thionyl chloride 8.1: pyridine; 4-(N,N-dimethlyamino)pyridine / diethyl ether / 0.33 h 9.1: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / benzene / 25 °C / Cooling with liquid nitrogen; Sealed tube; UV-irradiation View Scheme

1.1: thionyl chloride / 1 h / Reflux 2.1: 0.17 h / Reflux 3.1: sodium hydroxide 3.2: 20 h / Reflux 4.1: thionyl chloride 5.1: pyridine; 4-(N,N-dimethlyamino)pyridine / diethyl ether / 0.33 h 6.1: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / benzene / 25 °C / Cooling with liquid nitrogen; Sealed tube; UV-irradiation View Scheme

1.1: 0.17 h / Reflux 2.1: sodium hydroxide 2.2: 20 h / Reflux 3.1: thionyl chloride 4.1: pyridine; 4-(N,N-dimethlyamino)pyridine / diethyl ether / 0.33 h 5.1: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / benzene / 25 °C / Cooling with liquid nitrogen; Sealed tube; UV-irradiation View Scheme

sodium

diethyl ether; sodium