methanol; sodium hydroxide

1: sodium bicarbonate / H2O; diethyl ether / 16 h / 15 °C 2: 4-dimethylaminopyridone / acetonitrile / 2 h / Ambient temperature 3: α,α'-azobisisobutyronitrile, tributyltin hydride / toluene / 4 h / 70 °C 4: 61 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 1 h / Ambient temperature 5: 93 percent / pyridine / 24 h / 18 °C 6: pyridine / CH2Cl2 / 2 h / Ambient temperature 7: 60 percent / tributyltin hydride, α,α'-azobisisobutironitrile / toluene / 3 h / 70 °C 8: 1N NaOH / methanol / 5 h / Heating; pH = 9 View Scheme

1: 61 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 1 h / Ambient temperature 2: 93 percent / pyridine / 24 h / 18 °C 3: pyridine / CH2Cl2 / 2 h / Ambient temperature 4: 60 percent / tributyltin hydride, α,α'-azobisisobutironitrile / toluene / 3 h / 70 °C 5: 1N NaOH / methanol / 5 h / Heating; pH = 9 View Scheme

1: 93 percent / pyridine / 24 h / 18 °C 2: pyridine / CH2Cl2 / 2 h / Ambient temperature 3: 60 percent / tributyltin hydride, α,α'-azobisisobutironitrile / toluene / 3 h / 70 °C 4: 1N NaOH / methanol / 5 h / Heating; pH = 9 View Scheme

1: 68 percent / pyridine / 48 h / Ambient temperature 2: 73 percent / CrO3, pyridine, Ac2O / CH2Cl2 / 0.75 h / Ambient temperature 3: sodium bicarbonate / H2O; diethyl ether / 16 h / 15 °C 4: 4-dimethylaminopyridone / acetonitrile / 2 h / Ambient temperature 5: α,α'-azobisisobutyronitrile, tributyltin hydride / toluene / 4 h / 70 °C 6: 61 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 1 h / Ambient temperature 7: 93 percent / pyridine / 24 h / 18 °C 8: pyridine / CH2Cl2 / 2 h / Ambient temperature 9: 60 percent / tributyltin hydride, α,α'-azobisisobutironitrile / toluene / 3 h / 70 °C 10: 1N NaOH / methanol / 5 h / Heating; pH = 9 View Scheme

1: 4-dimethylaminopyridone / acetonitrile / 2 h / Ambient temperature 2: α,α'-azobisisobutyronitrile, tributyltin hydride / toluene / 4 h / 70 °C 3: 61 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 1 h / Ambient temperature 4: 93 percent / pyridine / 24 h / 18 °C 5: pyridine / CH2Cl2 / 2 h / Ambient temperature 6: 60 percent / tributyltin hydride, α,α'-azobisisobutironitrile / toluene / 3 h / 70 °C 7: 1N NaOH / methanol / 5 h / Heating; pH = 9 View Scheme

1: 60 percent / tributyltin hydride, α,α'-azobisisobutironitrile / toluene / 3 h / 70 °C 2: 1N NaOH / methanol / 5 h / Heating; pH = 9 View Scheme