sodium hydroxide in 1,4-dioxane 5 h; Ambient temperature;

1: p-toluenesulfonic acid 2: 1.46 g / EtOK / ethanol; diethyl ether / 34 h / Heating 3: 84 percent / HCl / ethanol / 3 h / 60 °C 4: 1.) Raney nickel, 2.) Raney nickel, H2 / 1.) EtOH, 35 deg C, 24 h, 2.) RT, 40 psi, 1 h 5: 1.) NaNO2, 80percent HOAc, 2.) NaN3 / 0 deg C 6: 79 percent / 1 M NaOH / dioxane / 5 h / Ambient temperature View Scheme

1: 1.46 g / EtOK / ethanol; diethyl ether / 34 h / Heating 2: 84 percent / HCl / ethanol / 3 h / 60 °C 3: 1.) Raney nickel, 2.) Raney nickel, H2 / 1.) EtOH, 35 deg C, 24 h, 2.) RT, 40 psi, 1 h 4: 1.) NaNO2, 80percent HOAc, 2.) NaN3 / 0 deg C 5: 79 percent / 1 M NaOH / dioxane / 5 h / Ambient temperature View Scheme

1: 84 percent / HCl / ethanol / 3 h / 60 °C 2: 1.) Raney nickel, 2.) Raney nickel, H2 / 1.) EtOH, 35 deg C, 24 h, 2.) RT, 40 psi, 1 h 3: 1.) NaNO2, 80percent HOAc, 2.) NaN3 / 0 deg C 4: 79 percent / 1 M NaOH / dioxane / 5 h / Ambient temperature View Scheme

1: 1.) NaNO2, 80percent HOAc, 2.) NaN3 / 0 deg C 2: 79 percent / 1 M NaOH / dioxane / 5 h / Ambient temperature View Scheme

1: 1.) Raney nickel, 2.) Raney nickel, H2 / 1.) EtOH, 35 deg C, 24 h, 2.) RT, 40 psi, 1 h 2: 1.) NaNO2, 80percent HOAc, 2.) NaN3 / 0 deg C 3: 79 percent / 1 M NaOH / dioxane / 5 h / Ambient temperature View Scheme