iodine in 1,4-dioxane T=45°C; 20 h;

1: 82 percent / I2 / dioxane / 20 h / 45 °C 2: 89 percent / LiAlH4 / diethyl ether / Heating 3: 78 percent / CrO3 / pyridine 4: 1.) NaH / 1.) DME View Scheme