potassium tert-butylate in tetrahydrofuran; methanol T=0°C; 0.0833333 h;

1.1: 87 percent / AlCl3 / CS2 / 8 h / 23 °C 2.1: hydrazine*monohydrate / bis-(2-hydroxy-ethyl) ether / 2 h / 120 °C 2.2: 94 percent / KOH / bis-(2-hydroxy-ethyl) ether / 3 h / 200 °C 3.1: N,N,N',N'-tetramethylethylenediamine; n-BuLi / toluene; hexane / 0.25 h / 0 °C 3.2: 57 percent / toluene; hexane / 1.33 h / 0 °C 4.1: 91 percent / potassium t-butoxide / methanol; tetrahydrofuran / 0.08 h / 0 °C View Scheme

1.1: 87 percent / AlCl3 / CS2 / 8 h / 23 °C 2.1: hydrazine*monohydrate / bis-(2-hydroxy-ethyl) ether / 2 h / 120 °C 2.2: 94 percent / KOH / bis-(2-hydroxy-ethyl) ether / 3 h / 200 °C 3.1: N,N,N',N'-tetramethylethylenediamine; n-BuLi / toluene; hexane / 0.25 h / 0 °C 3.2: 57 percent / toluene; hexane / 1.33 h / 0 °C 4.1: 91 percent / potassium t-butoxide / methanol; tetrahydrofuran / 0.08 h / 0 °C View Scheme

1.1: N,N,N',N'-tetramethylethylenediamine; n-BuLi / toluene; hexane / 0.25 h / 0 °C 1.2: 57 percent / toluene; hexane / 1.33 h / 0 °C 2.1: 91 percent / potassium t-butoxide / methanol; tetrahydrofuran / 0.08 h / 0 °C View Scheme

1.1: hydrazine*monohydrate / bis-(2-hydroxy-ethyl) ether / 2 h / 120 °C 1.2: 94 percent / KOH / bis-(2-hydroxy-ethyl) ether / 3 h / 200 °C 2.1: N,N,N',N'-tetramethylethylenediamine; n-BuLi / toluene; hexane / 0.25 h / 0 °C 2.2: 57 percent / toluene; hexane / 1.33 h / 0 °C 3.1: 91 percent / potassium t-butoxide / methanol; tetrahydrofuran / 0.08 h / 0 °C View Scheme