in pyridine Ambient temperature;

1: dimethyl sulfoxide, sodium hydride 2: LiAlH4 / tetrahydrofuran / 2 h / cooling 3: 96 percent / HCl, SnCl2 4: 84 percent / BBr3 / benzene / 0.75 h / Heating; deoxygenated solvents 5: 85 percent / pyridine / Ambient temperature View Scheme

1: 84 percent / BBr3 / benzene / 0.75 h / Heating; deoxygenated solvents 2: 85 percent / pyridine / Ambient temperature View Scheme

1: 1.) acetic anhydride, zinc chloride, 2.) potassium dichromate / 1.) reflux, acetic acid, 2 h, 2.) +H2O, reflux, 1 h 2: dimethyl sulfoxide, sodium hydride 3: LiAlH4 / tetrahydrofuran / 2 h / cooling 4: 96 percent / HCl, SnCl2 5: 84 percent / BBr3 / benzene / 0.75 h / Heating; deoxygenated solvents 6: 85 percent / pyridine / Ambient temperature View Scheme

1: 97 percent / aqueous potassium hydroxide, potassium permanganate / pyridine / 8 h / 95 - 100 °C 2: 98 percent / potassium hydroxide, copper sulfate, zinc dust / 20 h / Heating 3: 1.) acetic anhydride, zinc chloride, 2.) potassium dichromate / 1.) reflux, acetic acid, 2 h, 2.) +H2O, reflux, 1 h 4: dimethyl sulfoxide, sodium hydride 5: LiAlH4 / tetrahydrofuran / 2 h / cooling 6: 96 percent / HCl, SnCl2 7: 84 percent / BBr3 / benzene / 0.75 h / Heating; deoxygenated solvents 8: 85 percent / pyridine / Ambient temperature View Scheme

1: 98 percent / potassium hydroxide, copper sulfate, zinc dust / 20 h / Heating 2: 1.) acetic anhydride, zinc chloride, 2.) potassium dichromate / 1.) reflux, acetic acid, 2 h, 2.) +H2O, reflux, 1 h 3: dimethyl sulfoxide, sodium hydride 4: LiAlH4 / tetrahydrofuran / 2 h / cooling 5: 96 percent / HCl, SnCl2 6: 84 percent / BBr3 / benzene / 0.75 h / Heating; deoxygenated solvents 7: 85 percent / pyridine / Ambient temperature View Scheme

1: 96 percent / HCl, SnCl2 2: 84 percent / BBr3 / benzene / 0.75 h / Heating; deoxygenated solvents 3: 85 percent / pyridine / Ambient temperature View Scheme

1: LiAlH4 / tetrahydrofuran / 2 h / cooling 2: 96 percent / HCl, SnCl2 3: 84 percent / BBr3 / benzene / 0.75 h / Heating; deoxygenated solvents 4: 85 percent / pyridine / Ambient temperature View Scheme

2: 97 percent / aqueous potassium hydroxide, potassium permanganate / pyridine / 8 h / 95 - 100 °C 3: 98 percent / potassium hydroxide, copper sulfate, zinc dust / 20 h / Heating 4: 1.) acetic anhydride, zinc chloride, 2.) potassium dichromate / 1.) reflux, acetic acid, 2 h, 2.) +H2O, reflux, 1 h 5: dimethyl sulfoxide, sodium hydride 6: LiAlH4 / tetrahydrofuran / 2 h / cooling 7: 96 percent / HCl, SnCl2 8: 84 percent / BBr3 / benzene / 0.75 h / Heating; deoxygenated solvents 9: 85 percent / pyridine / Ambient temperature View Scheme

1: 86 percent 3: 97 percent / aqueous potassium hydroxide, potassium permanganate / pyridine / 8 h / 95 - 100 °C 4: 98 percent / potassium hydroxide, copper sulfate, zinc dust / 20 h / Heating 5: 1.) acetic anhydride, zinc chloride, 2.) potassium dichromate / 1.) reflux, acetic acid, 2 h, 2.) +H2O, reflux, 1 h 6: dimethyl sulfoxide, sodium hydride 7: LiAlH4 / tetrahydrofuran / 2 h / cooling 8: 96 percent / HCl, SnCl2 9: 84 percent / BBr3 / benzene / 0.75 h / Heating; deoxygenated solvents 10: 85 percent / pyridine / Ambient temperature View Scheme