1: With pyridinium tribromide; acetic acid in water T=20 - 50°C; 19 h; 2: With sodium hydroxide in water

1: With sodium tetrahydroborate T=55 - 60°C; 20 h; 2: With sodium hydroxide in water T=20°C;

sodium hydrogencarbonate in toluene 27 h; Heating / reflux;

1: hexamethylphosphorous triamide / CCl4 2: LiAlH4 View Scheme

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. 7: 85 percent / CCl4; tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -20 deg C, 30 min, 2.) R.T., 12 h. 8: lithium aluminum hydride / tetrahydrofuran / 12 h / Heating 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. 6: 85 percent / CCl4; tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -20 deg C, 30 min, 2.) R.T., 12 h. 7: lithium aluminum hydride / tetrahydrofuran / 12 h / Heating 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. 5: 85 percent / CCl4; tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -20 deg C, 30 min, 2.) R.T., 12 h. 6: lithium aluminum hydride / tetrahydrofuran / 12 h / Heating View Scheme

1: hexamethylphosphorous triamide / CCl4 2: LiAlH4 View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 12 h; Heating; Yield given;

1: NaBH3CN, acetic acid / ethanol / Ambient temperature 2: EtONa / ethanol / Ambient temperature View Scheme