1: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 2: 82 percent / triethylamine, 4-dimethyl-aminopyridine / CH2Cl2 / 10 h / Ambient temperature 3: 95 percent / benzoyl peroxiden, N-bromosuccinimide / CCl4 / Heating; Irradiation 4: 61 percent / mercuric acetate / 2 h / Heating 5: 86 percent / ammonia, methanol / 10 h / Ambient temperature 6: 78 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 7: 97 percent / p-toluenesulfonic acid / benzene / 4 h / Heating 8: 91 percent / sodium hydroxide, water / tetrahydrofuran / 4 h / 24 °C 9: 70 percent / pyridine, chromium trioxide / CH2Cl2 / 0.5 h / 23 °C 10: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 25 deg C, 1 h 11: 51 percent / benzene; methanol / 16 h / Heating 12: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 13: hydrochloric acid / methanol View Scheme

1: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 2: 96 percent / triethylamine, 4-dimethylaminopyridine / CH2Cl2 / 8 h / 22 °C 3: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl4 / Heating; Irradiation 4: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 °C 5: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 6: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 7: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 8: hexane; methanol / 14 h / Heating 9: hydrochloric acid / ethanol View Scheme

1: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 2: 96 percent / triethylamine, 4-dimethylaminopyridine / CH2Cl2 / 8 h / 22 °C 3: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl4 / Heating; Irradiation 4: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 °C 5: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 6: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C View Scheme

1: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 2: 96 percent / triethylamine, 4-dimethylaminopyridine / CH2Cl2 / 8 h / 22 °C 3: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl4 / Heating; Irradiation 4: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 °C 5: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 6: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 7: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 8: hexane; methanol / 14 h / Heating View Scheme

1: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 2: 82 percent / triethylamine, 4-dimethyl-aminopyridine / CH2Cl2 / 10 h / Ambient temperature 3: 95 percent / benzoyl peroxiden, N-bromosuccinimide / CCl4 / Heating; Irradiation 4: 61 percent / mercuric acetate / 2 h / Heating 5: 86 percent / ammonia, methanol / 10 h / Ambient temperature 6: 78 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 7: 97 percent / p-toluenesulfonic acid / benzene / 4 h / Heating 8: 91 percent / sodium hydroxide, water / tetrahydrofuran / 4 h / 24 °C 9: 70 percent / pyridine, chromium trioxide / CH2Cl2 / 0.5 h / 23 °C 10: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 25 deg C, 1 h 11: 51 percent / benzene; methanol / 16 h / Heating 12: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr View Scheme

1: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 2: 96 percent / triethylamine, 4-dimethylaminopyridine / CH2Cl2 / 8 h / 22 °C 3: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl4 / Heating; Irradiation 4: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 °C 5: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 6: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 7: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 8: hexane; methanol / 14 h / Heating 9: hydrochloric acid / ethanol 10: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme