lithium aluminium tetrahydride in diethylene glycol dimethyl ether T=140°C; 48 h;

hydrogenchloride in tetrahydrofuran 4 h; Heating;

1.1: SO3*pyridine / tetrahydrofuran / 1 h / 20 °C 1.2: 53 percent / LiAlH4 / tetrahydrofuran / 7 h / 20 °C 2.1: 85 percent / hydrochloric acid / tetrahydrofuran / 4 h / Heating View Scheme

1.1: 83 percent / DIBAL-H / CH2Cl2; toluene / 1 h / -20 °C 2.1: SO3*pyridine / tetrahydrofuran / 1 h / 20 °C 2.2: 53 percent / LiAlH4 / tetrahydrofuran / 7 h / 20 °C 3.1: 85 percent / hydrochloric acid / tetrahydrofuran / 4 h / Heating View Scheme

1.1: 43 percent / N-ethyldiisopropylamine / CH2Cl2 / 14 h / 20 °C 2.1: PCC / CH2Cl2 / 3 h / 20 °C 3.1: 1.29 g / NaH / benzene / 4 h / 20 °C 4.1: 83 percent / DIBAL-H / CH2Cl2; toluene / 1 h / -20 °C 5.1: SO3*pyridine / tetrahydrofuran / 1 h / 20 °C 5.2: 53 percent / LiAlH4 / tetrahydrofuran / 7 h / 20 °C 6.1: 85 percent / hydrochloric acid / tetrahydrofuran / 4 h / Heating View Scheme

1.1: PCC / CH2Cl2 / 3 h / 20 °C 2.1: 1.29 g / NaH / benzene / 4 h / 20 °C 3.1: 83 percent / DIBAL-H / CH2Cl2; toluene / 1 h / -20 °C 4.1: SO3*pyridine / tetrahydrofuran / 1 h / 20 °C 4.2: 53 percent / LiAlH4 / tetrahydrofuran / 7 h / 20 °C 5.1: 85 percent / hydrochloric acid / tetrahydrofuran / 4 h / Heating View Scheme

1: 1.) LiNH2 / 1.) liq. NH3, 1 h, 2.) THF, 3 h 2: 16percent H2SO4 / ethanol / 1 h / 50 °C 3: 95 percent / LiAlH4 / bis-(2-methoxy-ethyl) ether / 48 h / 140 °C View Scheme

1: 16percent H2SO4 / ethanol / 1 h / 50 °C 2: 95 percent / LiAlH4 / bis-(2-methoxy-ethyl) ether / 48 h / 140 °C View Scheme

1: conc. HCl / 3 h / 20 °C 2: 1.) LiNH2 / 1.) liq. NH3, 1 h, 2.) THF, 3 h 3: 16percent H2SO4 / ethanol / 1 h / 50 °C 4: 95 percent / LiAlH4 / bis-(2-methoxy-ethyl) ether / 48 h / 140 °C View Scheme

1: 85 percent / LiAlH4 / diethyl ether / 3 h / 40 °C 2: conc. HCl / 3 h / 20 °C 3: 1.) LiNH2 / 1.) liq. NH3, 1 h, 2.) THF, 3 h 4: 16percent H2SO4 / ethanol / 1 h / 50 °C 5: 95 percent / LiAlH4 / bis-(2-methoxy-ethyl) ether / 48 h / 140 °C View Scheme