n-butyllithium in tetrahydrofuran; hexane T=-78°C; 2 h;

1: 97 percent / p-TsOH / benzene 2: 97 percent / NaNH2 / H2O / 5 h / -33 °C 3: 82 percent / n-BuLi / hexane; tetrahydrofuran / 2 h / -78 °C View Scheme

1: ethanol 2: 1.) Mg, 2.) aq. HCl / 1.) ether, reflux, 2 h, 2.) ether, reflux, 30 min 3: 78 percent 4: BuLi / diethyl ether; hexane; tetrahydrofuran / 2 h / 0 °C 5: 2.1 g / diethyl ether; hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 12 h / 20 °C View Scheme

1: 1.) Mg, 2.) aq. HCl / 1.) ether, reflux, 2 h, 2.) ether, reflux, 30 min 2: 78 percent 3: BuLi / diethyl ether; hexane; tetrahydrofuran / 2 h / 0 °C 4: 2.1 g / diethyl ether; hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 12 h / 20 °C View Scheme

in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; diethyl ether; hexane T=20°C; 12 h;