1.1: 98 percent / NaH / dimethylformamide / 0.33 h / 20 °C 2.1: ozone / CH2Cl2 / 2.5 h / -78 °C 2.2: dimethyl sulfide / CH2Cl2 / 0.5 h / 20 °C 2.3: 54 percent / satd. aq. NaHCO3 / ethanol / Heating 3.1: 90 percent / conc. HCl / methanol / 0.67 h / 20 °C View Scheme

lithium aluminium tetrahydride in diethyl ether 0.75 h; Ambient temperature;

boron tribromide in dichloromethane T=-78°C;

1: 1.63 g / aluminium chloride / diethyl ether / 1.5 h / 15 °C / < 15 deg C 2: 490 mg / H2 / 5percent palladium-charcoal / ethyl acetate 3: 10.6 g / pyridine / 3.25 h / 80 - 90 °C 4: 12.52 g / N-bromosuccinimide / CCl4 / 0.58 h / Heating 5: acetonitrile / 2 h / Heating 6: triethylamine / toluene / 1.) reflux, 4 h, 2.) room temperature, 12 h 7: 90 percent / LiALH4 / diethyl ether / 0.75 h / Ambient temperature View Scheme

1: 490 mg / H2 / 5percent palladium-charcoal / ethyl acetate 2: 10.6 g / pyridine / 3.25 h / 80 - 90 °C 3: 12.52 g / N-bromosuccinimide / CCl4 / 0.58 h / Heating 4: acetonitrile / 2 h / Heating 5: triethylamine / toluene / 1.) reflux, 4 h, 2.) room temperature, 12 h 6: 90 percent / LiALH4 / diethyl ether / 0.75 h / Ambient temperature View Scheme

selenium(IV) oxide; dihydrogen peroxide

1: 10.6 g / pyridine / 3.25 h / 80 - 90 °C 2: 12.52 g / N-bromosuccinimide / CCl4 / 0.58 h / Heating 3: acetonitrile / 2 h / Heating 4: triethylamine / toluene / 1.) reflux, 4 h, 2.) room temperature, 12 h 5: 90 percent / LiALH4 / diethyl ether / 0.75 h / Ambient temperature View Scheme

1: 12.52 g / N-bromosuccinimide / CCl4 / 0.58 h / Heating 2: acetonitrile / 2 h / Heating 3: triethylamine / toluene / 1.) reflux, 4 h, 2.) room temperature, 12 h 4: 90 percent / LiALH4 / diethyl ether / 0.75 h / Ambient temperature View Scheme

1: acetonitrile / 2 h / Heating 2: triethylamine / toluene / 1.) reflux, 4 h, 2.) room temperature, 12 h 3: 90 percent / LiALH4 / diethyl ether / 0.75 h / Ambient temperature View Scheme

1: triethylamine / toluene / 1.) reflux, 4 h, 2.) room temperature, 12 h 2: 90 percent / LiALH4 / diethyl ether / 0.75 h / Ambient temperature View Scheme