1: 90 percent / 3N H2SO4 / dioxane / 4 h / Heating 2: 87 percent / LiAlH4, MeOH / tetrahydrofuran / 4 h / Heating 3: 49 percent / Br2, triphenylphosphite / CH2Cl2 / 3 h / Ambient temperature View Scheme

sulfuric acid in 1,4-dioxane 4 h; Heating;

1: 90 percent / 3N H2SO4 / dioxane / 4 h / Heating 2: 87 percent / LiAlH4, MeOH / tetrahydrofuran / 4 h / Heating 3: 49 percent / Br2, triphenylphosphite / CH2Cl2 / 3 h / Ambient temperature 4: 1.) Mg; 2.) CuBr / 1.) THF, 2h, reflux; 2.) THF, 2h, reflux 5: 91 percent / H2O, p-TosOH / methanol View Scheme

1: 90 percent / 3N H2SO4 / dioxane / 4 h / Heating 2: 87 percent / LiAlH4, MeOH / tetrahydrofuran / 4 h / Heating View Scheme

1: 90 percent / 3N H2SO4 / dioxane / 4 h / Heating 2: 87 percent / LiAlH4, MeOH / tetrahydrofuran / 4 h / Heating View Scheme