jones reagent in acetone T=-30°C; 5 h;

lithium hydroxide in tetrahydrofuran 3 h; Ambient temperature;

lithium hydroxide in methanol 12 h;

1: 84 percent / NaBH4 / ethanol / 0.42 h / 25 °C 2: triethylamine / 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / Ambient temperature 3: K2CO3 / methanol / 24 h / Ambient temperature 4: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h 5: 73 percent / benzene / 14 h / 120 °C / in a sealed tube 6: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C 7: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min 8: conc. HCl / methanol / 4.5 h / Heating 9: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme

1: triethylamine / 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / Ambient temperature 2: K2CO3 / methanol / 24 h / Ambient temperature 3: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h 4: 73 percent / benzene / 14 h / 120 °C / in a sealed tube 5: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C 6: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min 7: conc. HCl / methanol / 4.5 h / Heating 8: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme

1: K2CO3 / methanol / 24 h / Ambient temperature 2: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h 3: 73 percent / benzene / 14 h / 120 °C / in a sealed tube 4: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C 5: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min 6: conc. HCl / methanol / 4.5 h / Heating 7: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme

1: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h 2: 73 percent / benzene / 14 h / 120 °C / in a sealed tube 3: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C 4: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min 5: conc. HCl / methanol / 4.5 h / Heating 6: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme

1: 73 percent / benzene / 14 h / 120 °C / in a sealed tube 2: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C 3: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min 4: conc. HCl / methanol / 4.5 h / Heating 5: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme

1: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C 2: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min 3: conc. HCl / methanol / 4.5 h / Heating 4: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme

1: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min 2: conc. HCl / methanol / 4.5 h / Heating 3: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme