sodium hydride; tert-butyl alcohol in toluene T=80°C; 1 h;

toluene-4-sulfonic acid T=110°C; 1.5 h;

2: 78 percent / NaH / t-BuOH / toluene / 1 h / 80 °C View Scheme

1: 95 percent / NaBH4 / dimethylsulfoxide / 1 h / Ambient temperature 2: 1.) NaOCH3, TiCl3, CH3CO2NH4, 6 N HCl, 2.) Ac2O, HClO4 / 1.) THF, H2O, RT, 1.5 h, nitrogen atmosphere, 2.) EtOAc, RT, 1 h View Scheme

1: 90 percent / triethylamine / dimethylsulfoxide / 48 h / Ambient temperature 2: 95 percent / NaBH4 / dimethylsulfoxide / 1 h / Ambient temperature 3: 1.) NaOCH3, TiCl3, CH3CO2NH4, 6 N HCl, 2.) Ac2O, HClO4 / 1.) THF, H2O, RT, 1.5 h, nitrogen atmosphere, 2.) EtOAc, RT, 1 h View Scheme

1: 1.) sodium hydroxide; 2.) 6 N hydrochloric acid / 1.) water, 50-60 deg C, 2 h; 2.) heating, 1 h 2: diethyl ether / 1 h / Heating 3: 1.6 g / hydrogen chloride(gas), conc. hydrogen chloride / dioxane / 2 h / 50 - 60 °C 4: 0.5 g / selenium dioxide / xylene / 6 h / Heating 5: 1.) N-bromosuccinimide, benzoyl peroxide; 2.) triethylamine / 1.) carbon tetrachloride, irradiation, reflux, 2 h; 2.) reflux, 8 h View Scheme

1: 1.6 g / hydrogen chloride(gas), conc. hydrogen chloride / dioxane / 2 h / 50 - 60 °C 2: 0.5 g / selenium dioxide / xylene / 6 h / Heating 3: 1.) N-bromosuccinimide, benzoyl peroxide; 2.) triethylamine / 1.) carbon tetrachloride, irradiation, reflux, 2 h; 2.) reflux, 8 h View Scheme

1: diethyl ether / 1 h / Heating 2: 1.6 g / hydrogen chloride(gas), conc. hydrogen chloride / dioxane / 2 h / 50 - 60 °C 3: 0.5 g / selenium dioxide / xylene / 6 h / Heating 4: 1.) N-bromosuccinimide, benzoyl peroxide; 2.) triethylamine / 1.) carbon tetrachloride, irradiation, reflux, 2 h; 2.) reflux, 8 h View Scheme

1: 14 g / ethanol; benzene / 2 h / Ambient temperature 2: 1.) sodium hydroxide; 2.) 6 N hydrochloric acid / 1.) water, 50-60 deg C, 2 h; 2.) heating, 1 h 3: diethyl ether / 1 h / Heating 4: 1.6 g / hydrogen chloride(gas), conc. hydrogen chloride / dioxane / 2 h / 50 - 60 °C 5: 0.5 g / selenium dioxide / xylene / 6 h / Heating 6: 1.) N-bromosuccinimide, benzoyl peroxide; 2.) triethylamine / 1.) carbon tetrachloride, irradiation, reflux, 2 h; 2.) reflux, 8 h View Scheme

1: 0.5 g / selenium dioxide / xylene / 6 h / Heating 2: 1.) N-bromosuccinimide, benzoyl peroxide; 2.) triethylamine / 1.) carbon tetrachloride, irradiation, reflux, 2 h; 2.) reflux, 8 h View Scheme