1: 91 percent / dimethylsulfoxide; 1,2-dimethoxy-ethane 2: 90 percent / NaH / dimethylsulfoxide View Scheme

1: 91 percent / dimethylsulfoxide; 1,2-dimethoxy-ethane 2: 89 percent / NaH View Scheme

1: 56 percent / tetrahydrofuran 2: 96 percent / Na/Hg View Scheme

1: 100 percent / LAH / diethyl ether / 0.5 h / 0 °C 2: 77 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / 0 °C 3: 1.) 2.3 M tert-butyllihium in pentane / 1.) THF, -78 deg C, 3 h, 2.) 10 min 4: 70percent aq. perchloric acid / dioxane / 0.5 h / Ambient temperature View Scheme

1: 91 percent / dimethylsulfoxide; 1,2-dimethoxy-ethane 2: 90 percent / NaH / dimethylsulfoxide 3: 92 percent / Na/Hg View Scheme

1: 91 percent / 1.) sodium hydride / dimethylsulfoxide; 1,2-dimethoxy-ethane / 65 °C / 1.) 1 h; 2.) 1.5 h 2: 792 mg / potassium carbonate / dimethylformamide / 31 h / 100 °C 3: 166 mg / sodium amalgam/ disodium hydrogen phosphate / methanol / 0 deg C, 1 h then rt., 16 h View Scheme

1: 86 percent / LAH / diethyl ether / 0.5 h / 0 °C 2: 71 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / 0 °C 3: 1.) magnesium / 1.) THF, RT, 1 h, 2.) RT, 5 min 4: 1.) p-toluenesulfonic acid, 2.) 6 N aq. HCl / 1.) acetone, RT, 3 h, 2.) THF, reflux, 5 h View Scheme

1: 86 percent / LAH / diethyl ether / 0.5 h / 0 °C 2: 71 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / 0 °C 3: 1.) magnesium / 1.) ether, 2.) RT, 15 min 4: triethylamine / CH2Cl2 / 0.08 h / 0 °C 5: triethylamine / CH2Cl2 / 0.33 h / Ambient temperature View Scheme