sodium tetrahydroborate; hydrogen; nickel diacetate; ethylenediamine in ethanol

1.1: 70 percent / lithium amide / liquid ammonia; tetrahydrofuran; hexamethylphosphoric acid triamide / 6 h 2.1: hydrogen / Lindlar catalyst / ethanol 3.1: 85 percent / I2; imidazole; triphenylphosphine / acetonitrile; diethyl ether / 0.75 h / 20 °C 4.1: 6 g / acetonitrile / 48 h / 60 °C 5.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / 0 °C 5.2: TsOH / methanol / 1 h / 20 °C View Scheme

1: With n-butyllithium in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane T=0°C; 2 h; 2: With toluene-4-sulfonic acid in methanol T=20°C; 1 h;

phosphoric acid in methanol 5 h; Ambient temperature;

1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / 0 °C 2: TsOH / methanol View Scheme

1.1: 85 percent / I2; imidazole; triphenylphosphine / acetonitrile; diethyl ether / 0.75 h / 20 °C 2.1: 6 g / acetonitrile / 48 h / 60 °C 3.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / 0 °C 3.2: TsOH / methanol / 1 h / 20 °C View Scheme

1.1: 6 g / acetonitrile / 48 h / 60 °C 2.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / 0 °C 2.2: TsOH / methanol / 1 h / 20 °C View Scheme

1: 1.) C2H5MgBr, 2.) cuprous chloride / 1.) THF, reflux, 3 h, 2.) a). 20 deg C, 2 h, b). 65 deg C, 12 h 2: 90 percent / hydrogen, nickel acetate, sodium borohydride, ethylenediamine / ethanol View Scheme

1: 1.) C2H5MgBr, 2.) cuprous chloride / 1.) THF, reflux, 3 h, 2.) a). 20 deg C, 2 h, b). 65 deg C, 12 h 2: 90 percent / hydrogen, nickel acetate, sodium borohydride, ethylenediamine / ethanol View Scheme