sodium hydroxide in 1,4-dioxane; water 1 h;

hydrogen; rhodium on alumina in ethanol P=3040 - 3800 Torr; 16 h; Yield given;

1: 99.5 percent / NaHCO3 / dimethylformamide / 120 h 2: 98.2 percent / dihydrogen / 5percent Rh/Al2O3 / methanol / 18 h / 1551.4 - 2844.3 Torr 3: 80 percent / diisobutylaluminum hydride (Dibal), CH3OH / toluene; hexane / 2 h / -78 °C 4: 1.) diisopropylamine, n-BuLi / 1.) dioxane, hexane, -78 deg C, 15 min, 2.) THF, dioxane, hexane, -78 deg C, 5 min 5: 97 percent / 2 N NaOH / dioxane; H2O / 1 h View Scheme

1: 98.2 percent / dihydrogen / 5percent Rh/Al2O3 / methanol / 18 h / 1551.4 - 2844.3 Torr 2: 80 percent / diisobutylaluminum hydride (Dibal), CH3OH / toluene; hexane / 2 h / -78 °C 3: 1.) diisopropylamine, n-BuLi / 1.) dioxane, hexane, -78 deg C, 15 min, 2.) THF, dioxane, hexane, -78 deg C, 5 min 4: 97 percent / 2 N NaOH / dioxane; H2O / 1 h View Scheme

1: 1.) diisopropylamine, n-BuLi / 1.) dioxane, hexane, -78 deg C, 15 min, 2.) THF, dioxane, hexane, -78 deg C, 5 min 2: 97 percent / 2 N NaOH / dioxane; H2O / 1 h View Scheme

1: 96 percent / aq. potassium hydroxide / dioxane / 8 h / 0 °C 2: H2 / 5percent Rh-Al2O3 / ethanol / 16 h / 3040 - 3800 Torr View Scheme

1: 97 percent / H2 / RuBr2<(R)-binap> / ethanol / 145 h / 20 °C / 76000.1 Torr 2: 96 percent / aq. potassium hydroxide / dioxane / 8 h / 0 °C 3: H2 / 5percent Rh-Al2O3 / ethanol / 16 h / 3040 - 3800 Torr View Scheme

1: 80 percent / diisobutylaluminum hydride (Dibal), CH3OH / toluene; hexane / 2 h / -78 °C 2: 1.) diisopropylamine, n-BuLi / 1.) dioxane, hexane, -78 deg C, 15 min, 2.) THF, dioxane, hexane, -78 deg C, 5 min 3: 97 percent / 2 N NaOH / dioxane; H2O / 1 h View Scheme

1: 96 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 2: 4N HCl / dioxane / 0.5 h / Ambient temperature 3: 91 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 4: 4N HCl / dioxane / 0.5 h / Ambient temperature 5: 71 percent / DEPC, triethylamine / tetrahydrofuran / 8 h / 0 °C View Scheme