sodium acetate; pyridinium chlorochromate in dichloromethane 0.166667 h;

1: 99 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 2: 73 percent / LiAlH4 / tetrahydrofuran / 1) 0 deg C, 2) reflux, 0,5 h 3: pyridine / 5 °C 4: NaI / acetone / 3 h / Ambient temperature 5: 80 percent / toluene; acetonitrile / 48 h / 60 °C 6: 1) n-butyllithium / 1) THF, 0 deg C, 30 min, 2) THF/HMPA, 0 deg C, 2 h 7: 95 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.17 h View Scheme

1: 78 percent / Dibal-H / toluene / 1 h / -78 °C 2: 1) n-butyllithium / 1) THF, 0 deg C, 30 min, 2) THF/HMPA, 0 deg C, 2 h 3: 95 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.17 h View Scheme

1: 1) n-butyllithium / 1) THF, 0 deg C, 30 min, 2) THF/HMPA, 0 deg C, 2 h 2: 95 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.17 h View Scheme

1: 99 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 2: 73 percent / LiAlH4 / tetrahydrofuran / 1) 0 deg C, 2) reflux, 0,5 h 3: pyridine / 5 °C 4: NaI / acetone / 3 h / Ambient temperature 5: 80 percent / toluene; acetonitrile / 48 h / 60 °C 6: 1) n-butyllithium / 1) THF, 0 deg C, 30 min, 2) THF/HMPA, 0 deg C, 2 h 7: 95 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.17 h View Scheme

1: 80 percent / toluene; acetonitrile / 48 h / 60 °C 2: 1) n-butyllithium / 1) THF, 0 deg C, 30 min, 2) THF/HMPA, 0 deg C, 2 h 3: 95 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.17 h View Scheme

1: NaI / acetone / 3 h / Ambient temperature 2: 80 percent / toluene; acetonitrile / 48 h / 60 °C 3: 1) n-butyllithium / 1) THF, 0 deg C, 30 min, 2) THF/HMPA, 0 deg C, 2 h 4: 95 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.17 h View Scheme

1: 73 percent / LiAlH4 / tetrahydrofuran / 1) 0 deg C, 2) reflux, 0,5 h 2: pyridine / 5 °C 3: NaI / acetone / 3 h / Ambient temperature 4: 80 percent / toluene; acetonitrile / 48 h / 60 °C 5: 1) n-butyllithium / 1) THF, 0 deg C, 30 min, 2) THF/HMPA, 0 deg C, 2 h 6: 95 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.17 h View Scheme

1: pyridine / 5 °C 2: NaI / acetone / 3 h / Ambient temperature 3: 80 percent / toluene; acetonitrile / 48 h / 60 °C 4: 1) n-butyllithium / 1) THF, 0 deg C, 30 min, 2) THF/HMPA, 0 deg C, 2 h 5: 95 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.17 h View Scheme