hydrogenchloride in tetrahydrofuran T=25°C; 1 h;

1: 36 percent / 1) NaOEt / ethanol / 1) 20 deg C, 30 min, 2) reflux, 4.5 h 2: 65 percent / hydrogen / 11percent Pd/C / diethyl ether / 24 h / 1520 Torr 3: 85 percent / CrO3, H2SO4 / acetone / 2 h / 0 °C 4: p-TsOH / methanol / 1.5 h / 25 °C 5: 96 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 6: 95 percent / 6M aq. HCl / tetrahydrofuran / 1 h / 25 °C View Scheme