lithium aluminium tetrahydride in diethyl ether 5 h; Heating;

1: 6-bromo-n-caproic acid With 1-methyl-pyrrolidin-2-one; 1,1-dimethylethylmagnesium chloride in tetrahydrofuran T=-78°C; 0.166667 h; Inert atmosphere; 2: sec-butylmagnesium chloride With buta-1,3-diene; nickel dichloride in tetrahydrofuran P=760.051 Torr; 1 h; Inert atmosphereCooling with ice;

1: 50 percent / diethyl ether / 4 h / Heating 2: 53 percent / HCl / 2.5 h / Heating 3: 1.) hydrazine hydrate, 2.) NaOH, H2O / 1.) diethyleneglycol, reflux, 1 h, 2.) diethyleneglycol, a) reflux, 2 h, b) 195 to 200 deg C, 2 h View Scheme

1: 50 percent / diethyl ether / 4 h / Heating 2: 53 percent / HCl / 2.5 h / Heating 3: 1.) hydrazine hydrate, 2.) NaOH, H2O / 1.) diethyleneglycol, reflux, 1 h, 2.) diethyleneglycol, a) reflux, 2 h, b) 195 to 200 deg C, 2 h View Scheme

sodium hydroxide; water; hydrazine hydrate 1.) diethyleneglycol, reflux, 1 h, 2.) diethyleneglycol, a) reflux, 2 h, b) 195 to 200 deg C, 2 h; Yield given. Multistep reaction;

1: 53 percent / HCl / 2.5 h / Heating 2: 1.) hydrazine hydrate, 2.) NaOH, H2O / 1.) diethyleneglycol, reflux, 1 h, 2.) diethyleneglycol, a) reflux, 2 h, b) 195 to 200 deg C, 2 h View Scheme