pyridinium chlorochromate in dichloromethane 1.5 h; Ambient temperature;

silica gel; Bobbitt's oxidant in dichloromethane

(i) SOCl2, (ii) diglyme, Li<AlH(OtBu)3>; Multistep reaction;

1: 25percent aq. NaOH 2: LiAlH4 / diethyl ether / 2.5 h / Heating 3: fuming sulfuric acid, 96percent aq. H2SO4 / 2 h / 20 °C 4: LiAlH4 / diethyl ether / 2 h / Heating 5: pyridinium fluorochromate / CH2Cl2 / Ambient temperature View Scheme

1: fuming sulfuric acid, 96percent aq. H2SO4 / 2 h / 20 °C 2: LiAlH4 / diethyl ether / 2 h / Heating 3: pyridinium fluorochromate / CH2Cl2 / Ambient temperature View Scheme

1: LiAlH4 / diethyl ether / 2.5 h / Heating 2: fuming sulfuric acid, 96percent aq. H2SO4 / 2 h / 20 °C 3: LiAlH4 / diethyl ether / 2 h / Heating 4: pyridinium fluorochromate / CH2Cl2 / Ambient temperature View Scheme

1: 1 h / Heating 2: 1) NaBH4, Sn(CH3)3Cl / 1) EtOH, below 15 deg C, irradiation, 3 h, 2) MeCOMe, 15 min 3: 25percent aq. NaOH 4: LiAlH4 / diethyl ether / 2.5 h / Heating 5: fuming sulfuric acid, 96percent aq. H2SO4 / 2 h / 20 °C 6: LiAlH4 / diethyl ether / 2 h / Heating 7: pyridinium fluorochromate / CH2Cl2 / Ambient temperature View Scheme

1: SOCl2 / 2 h / Heating 2: 1 h / Heating 3: 1) NaBH4, Sn(CH3)3Cl / 1) EtOH, below 15 deg C, irradiation, 3 h, 2) MeCOMe, 15 min 4: 25percent aq. NaOH 5: LiAlH4 / diethyl ether / 2.5 h / Heating 6: fuming sulfuric acid, 96percent aq. H2SO4 / 2 h / 20 °C 7: LiAlH4 / diethyl ether / 2 h / Heating 8: pyridinium fluorochromate / CH2Cl2 / Ambient temperature View Scheme

1: 1) NaBH4, Sn(CH3)3Cl / 1) EtOH, below 15 deg C, irradiation, 3 h, 2) MeCOMe, 15 min 2: 25percent aq. NaOH 3: LiAlH4 / diethyl ether / 2.5 h / Heating 4: fuming sulfuric acid, 96percent aq. H2SO4 / 2 h / 20 °C 5: LiAlH4 / diethyl ether / 2 h / Heating 6: pyridinium fluorochromate / CH2Cl2 / Ambient temperature View Scheme