1: 1-Ethyl-1H-indol With n-butyllithium in tetrahydrofuran; hexane T=0 - 25°C; 1.5 h; 2: N,N-dimethyl-formamide in tetrahydrofuran; hexane T=-78°C; 1 h;

1.1: sulfuric acid / 24 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 4.1: manganese(IV) oxide / dichloromethane / 12 h / Reflux View Scheme

manganese(IV) oxide in dichloromethane 12 h; Reflux;

1.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3.1: manganese(IV) oxide / dichloromethane / 12 h / Reflux View Scheme

1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: manganese(IV) oxide / dichloromethane / 12 h / Reflux View Scheme

1.1: potassium hydroxide / N,N-dimethyl-formamide / 0.33 h / 0 °C 1.2: 1 h / 0 - 20 °C 2.1: n-butyllithium / diethyl ether / 3 h / 20 °C / |Reflux 2.2: 3 h / |Reflux View Scheme

n-butyllithium; N-lithium N'-methylpiperazide in diethyl ether; hexane var. lithium compounds, temp, times and solvents; Product distribution;