lithium borohydride in ethylene glycol dimethyl ether 1.) -78 deg C; 2.) room temp., 2 h;

1: 73 percent / 5percent aq NaOH / H2O / 16 h / Ambient temperature 2: 63 percent / K2S2O8, AgNO3 / H2O / 1.) 90-100 deg C; 2.) room temp. 16 h 3: 40 percent / dimethylformamide / 96 h / Ambient temperature 4: 90 percent / NaOH / methanol; dioxane; H2O / 16 h / 40 °C 5: 1.) Triethylamine; 2.) Hydroxybenztriazole, DCC / DMF, room temp., 16 h 6: 63 percent / LiBH4 / 1,2-dimethoxy-ethane / 1.) -78 deg C; 2.) room temp., 2 h View Scheme

1: 63 percent / K2S2O8, AgNO3 / H2O / 1.) 90-100 deg C; 2.) room temp. 16 h 2: 40 percent / dimethylformamide / 96 h / Ambient temperature 3: 90 percent / NaOH / methanol; dioxane; H2O / 16 h / 40 °C 4: 1.) Triethylamine; 2.) Hydroxybenztriazole, DCC / DMF, room temp., 16 h 5: 63 percent / LiBH4 / 1,2-dimethoxy-ethane / 1.) -78 deg C; 2.) room temp., 2 h View Scheme

1: 40 percent / dimethylformamide / 96 h / Ambient temperature 2: 90 percent / NaOH / methanol; dioxane; H2O / 16 h / 40 °C 3: 1.) Triethylamine; 2.) Hydroxybenztriazole, DCC / DMF, room temp., 16 h 4: 63 percent / LiBH4 / 1,2-dimethoxy-ethane / 1.) -78 deg C; 2.) room temp., 2 h View Scheme

1: 87 percent / Thionyl chloride 2: 1.) Triethylamine; 2.) Hydroxybenztriazole, DCC / DMF, room temp., 16 h 3: 63 percent / LiBH4 / 1,2-dimethoxy-ethane / 1.) -78 deg C; 2.) room temp., 2 h View Scheme