1: 89 percent / dimethylformamide / 3 h / 65 - 70 °C 2: 97 percent / sodium hydroxide / tetra-n-butylammonium hydrogen sulfate / CH2Cl2 / 0.5 h / 15 °C 3: 93 percent / hydrogen / 10percent palladium on charcoal / ethyl acetate / 12 h / 1551.4 Torr / Ambient temperature 4: thionyl chloride / CH2Cl2 / 12 h / Heating 5: triethylamine / tetrahydrofuran; diethyl ether / 3 h / 0 °C 6: 1.) silver benzoate, triethylamine, 2.) sodium hydroxide / 1.) 99percent ethanol, reflux, 1 h 15 min, 2.) methanol, water, 60-65 deg C, 4 h. View Scheme

1: 97 percent / sodium hydroxide / tetra-n-butylammonium hydrogen sulfate / CH2Cl2 / 0.5 h / 15 °C 2: 93 percent / hydrogen / 10percent palladium on charcoal / ethyl acetate / 12 h / 1551.4 Torr / Ambient temperature 3: thionyl chloride / CH2Cl2 / 12 h / Heating 4: triethylamine / tetrahydrofuran; diethyl ether / 3 h / 0 °C 5: 1.) silver benzoate, triethylamine, 2.) sodium hydroxide / 1.) 99percent ethanol, reflux, 1 h 15 min, 2.) methanol, water, 60-65 deg C, 4 h. View Scheme

1: 93 percent / hydrogen / 10percent palladium on charcoal / ethyl acetate / 12 h / 1551.4 Torr / Ambient temperature 2: thionyl chloride / CH2Cl2 / 12 h / Heating 3: triethylamine / tetrahydrofuran; diethyl ether / 3 h / 0 °C 4: 1.) silver benzoate, triethylamine, 2.) sodium hydroxide / 1.) 99percent ethanol, reflux, 1 h 15 min, 2.) methanol, water, 60-65 deg C, 4 h. View Scheme

1: triethylamine / tetrahydrofuran; diethyl ether / 3 h / 0 °C 2: 1.) silver benzoate, triethylamine, 2.) sodium hydroxide / 1.) 99percent ethanol, reflux, 1 h 15 min, 2.) methanol, water, 60-65 deg C, 4 h. View Scheme

1: thionyl chloride / CH2Cl2 / 12 h / Heating 2: triethylamine / tetrahydrofuran; diethyl ether / 3 h / 0 °C 3: 1.) silver benzoate, triethylamine, 2.) sodium hydroxide / 1.) 99percent ethanol, reflux, 1 h 15 min, 2.) methanol, water, 60-65 deg C, 4 h. View Scheme

sodium hydroxide; silver benzoate; triethylamine 1.) 99percent ethanol, reflux, 1 h 15 min, 2.) methanol, water, 60-65 deg C, 4 h.; Yield given. Multistep reaction;

potassium hydroxide

1: Na2CO3; ethanol 2: aqueous ethanol KOH View Scheme

1: hexamethylphosphorous triamide / CCl4 2: LiAlH4 View Scheme