2: 82 percent / LiAlH4 / tetrahydrofuran / 0 °C 3: 94 percent / N-Chlorosuccinimide, dimethyl sulfide / 1.) toluene, -23 deg C, 2h; 2.) toluene, triethylamine, -23 deg C, 10 min. 4: 94 percent / n-BuLi / tetrahydrofuran / 1 h / Heating 5: 89 percent / 30percent H2O2 / methanol / 12 h / Ambient temperature 6: 90 percent / NaHCO3 / toluene / 2 h / Heating View Scheme

pyridine 12 h; Ambient temperature;

1: 83 percent / Hg(OAc)2 / 12 h / Heating 2: 81 percent / xylene / 3 h / Heating 3: 80 percent / diethyl ether / 0 °C 4: 98 percent / pyridine / 12 h / Ambient temperature View Scheme

1: 81 percent / xylene / 3 h / Heating 2: 80 percent / diethyl ether / 0 °C 3: 98 percent / pyridine / 12 h / Ambient temperature View Scheme

1: 80 percent / diethyl ether / 0 °C 2: 98 percent / pyridine / 12 h / Ambient temperature View Scheme

2: 82 percent / LiAlH4 / tetrahydrofuran / 0 °C 3: 94 percent / N-Chlorosuccinimide, dimethyl sulfide / 1.) toluene, -23 deg C, 2h; 2.) toluene, triethylamine, -23 deg C, 10 min. 4: 94 percent / n-BuLi / tetrahydrofuran / 1 h / Heating 5: 89 percent / 30percent H2O2 / methanol / 12 h / Ambient temperature 6: 70 percent / (CF3CO)2O / 72 h / Ambient temperature 7: 74 percent / NasBH4 / aq. ethanol / 12 h / Ambient temperature 8: 79 percent / vanadyl acetylacetonate, 45percent tert-butylhydroperoxide / benzene / 2 h / Heating 9: 34 percent / CrO3-2py complex / CH2Cl2 / 1.5 h / Ambient temperature View Scheme

Yield given. Multistep reaction;

2: 82 percent / LiAlH4 / tetrahydrofuran / 0 °C 3: 94 percent / N-Chlorosuccinimide, dimethyl sulfide / 1.) toluene, -23 deg C, 2h; 2.) toluene, triethylamine, -23 deg C, 10 min. 4: 1.) lithium isopropylamide; 2.) oxalic acid / 1.) ether, room temp.; 2.) ether, room temp., 5h View Scheme

2: 82 percent / LiAlH4 / tetrahydrofuran / 0 °C View Scheme

2: 82 percent / LiAlH4 / tetrahydrofuran / 0 °C 3: 94 percent / N-Chlorosuccinimide, dimethyl sulfide / 1.) toluene, -23 deg C, 2h; 2.) toluene, triethylamine, -23 deg C, 10 min. View Scheme