1: 99 percent / SnCl4 / CH2Cl2 / 24 h / Ambient temperature 2: 85 percent / NaOH / dioxane; H2O / 2 h / Ambient temperature 3: 73 percent / diphenylphosphorylazide, Et3N / 18 h / 80 °C 4: 81 percent / Raney-Nickel / methanol / 4 h / Heating 5: NaOH / dioxane; H2O / 1 h / Ambient temperature View Scheme

hydrogenchloride; methanol; ammonium chloride 1.) MeOH, from 55 to 60 deg C, 2.5 h, 2.) 60 deg C, 3 h; Multistep reaction. Yields of byproduct given;