thionyl chloride 18 h; Inert atmosphereReflux;

1: sodium hydrogencarbonate / 1,4-dioxane; water / 0 - 20 °C 2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 20 °C 3: lithium borohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme

1: 69.6 percent / Et3N / dioxane; H2O / 15 h / 50 °C 2: 81 percent / LiAlH4 / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 15 h View Scheme

1: 69.6 percent / Et3N / dioxane; H2O / 15 h / 50 °C 2: 81 percent / LiAlH4 / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 15 h 3: pyridine / 1.) 0 deg C, 2.) stored in the refrigerator for 5 days 4: 63.5 percent / 1.) Na/NH3 (liq.) / 1.) THF, temperature of liquid NH3, 2.) room temperature, 18.5 h View Scheme

1: 69.6 percent / Et3N / dioxane; H2O / 15 h / 50 °C 2: 81 percent / LiAlH4 / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 15 h 3: pyridine / 1.) 0 deg C, 2.) stored in the refrigerator for 5 days 4: 63.5 percent / 1.) Na/NH3 (liq.) / 1.) THF, temperature of liquid NH3, 2.) room temperature, 18.5 h 5: CF3COOH / 0.5 h / 0 °C View Scheme

1: 1.) oxalyl chloride, DMF, 2.) triethylamine / 1.) CH2Cl2, reflux, 40 min, 2.) THF, 0 deg C, 30 min 2: 1.) Na2S2SO4, 2.) aq. HCl / 1.) THF, H2O, room temp., 1.5 d, 2.) THF, H2O, room temp., 2 d 3: 89 percent / H2 / Pd/C / methanol / 5 h / 60 °C / 2068.6 Torr 4: 79.4 percent / 24 h / Heating 5: 70 percent / oxalyl chloride, DMSO / CH2Cl2 / 1 h / -78 °C 6: 90 percent / pyridine / CH2Cl2 / 3 h / Ambient temperature 7: 50 percent / DABCO / (CH3CN)2PdCl2 / methanol / 45 °C 8: 99 percent / NaBH4 / methanol / 4.5 h 9: 0.1 M aq. HCl / 2 h / Ambient temperature View Scheme

triethylamine in ethanol; dichloromethane T=0 - 20°C; 16.25 h;

triethylamine in 1,4-dioxane; water T=50°C; 15 h;