1: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h 2: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 3: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 4: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 5: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 6: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 7: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 8: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 9: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C View Scheme

1: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 2: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 3: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 4: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 5: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 6: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 7: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C View Scheme

1: With boron trifluoride diethyl etherate in diethyl ether; dichloromethane T=20°C; 0.00416667 h; 2: With Dess-Martin periodane in dichloromethane T=20°C; 0.5 h;

toluene-4-sulfonic acid in acetone 12 h; Ambient temperature; Yield given;

1: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature 2: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 3: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 4: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature View Scheme

1: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 2: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 3: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature View Scheme

1: 92 percent / HCl / acetone; H2O 2: boron trifluoride diethyl ether / methanol / 1 h / Ambient temperature 3: 87 percent / Li, ethylamine / tetrahydrofuran / 0.5 h / -35 - -30 °C 4: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature 5: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 6: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 7: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature View Scheme

1: 87 percent / Li, ethylamine / tetrahydrofuran / 0.5 h / -35 - -30 °C 2: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature 3: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 4: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 5: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature View Scheme

1: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 2: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature View Scheme

1: boron trifluoride diethyl ether / methanol / 1 h / Ambient temperature 2: 87 percent / Li, ethylamine / tetrahydrofuran / 0.5 h / -35 - -30 °C 3: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature 4: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 5: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 6: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature View Scheme