pyridinium p-toluenesulfonate in hexane; dichloromethane; ethyl acetate

pyridinium p-toluenesulfonate in dichloromethane 4 h; Ambient temperature;

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: 59 percent / (dimethylamino)trimethylsilane, (dimethylamino)sulfur trifluoride / CCl3F / 1) -78 deg C, 45 min, 2) room temperature, 1h 7: 82 percent / pyridinium p-toluenesulfonate / methanol / 3 h / 55 °C 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 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