n-butyllithium in methanol; ice-water; hexane; N,N-dimethyl-formamide

manganese(IV) oxide in dichloromethane 5 h; Reflux;

diisobutylaluminium hydride in dichloromethane T=-70°C; 3 h;

diisobutylaluminium hydride in dichloromethane T=-60°C;

1: 93 percent / NaHCO3 / ethanol; H2O / 9 h / Heating 2: 62 percent / LiAlH4 / tetrahydrofuran / 3 h 3: 59 percent / MnO2 / CHCl3 / 1.5 h / Heating View Scheme

1: 1) conc. HCl, 2) NaHCO3 / 1) H2O, a) r.t., 2.5 h, b) 80 deg C, 40 min, 2) r.t., overnight 2: 17.2 percent / diisobutylaluminium hydride / CH2Cl2 / -60 °C View Scheme

1: 11.9 percent / 1) n-butylamine, 1) ethylamine / ethanol / 32 h / Heating 2: 51.2 percent / Fe powder, FeCl2*(H2O)x, conc. HCl / ethanol; H2O / 1 h / Heating 3: 74.5 percent / dimethylformamide / 1 h / 80 °C View Scheme

1: 11.9 percent / 1) n-butylamine, 1) ethylamine / ethanol / 32 h / Heating 2: 51.2 percent / Fe powder, FeCl2*(H2O)x, conc. HCl / ethanol; H2O / 1 h / Heating 3: 74.5 percent / dimethylformamide / 1 h / 80 °C 4: 50.9 percent / NaOCH3 / dimethylformamide / 12 h / 80 - 90 °C View Scheme