hydrogen; palladium on activated charcoal in toluene 6 h;

1: 75 percent / H2 / 5percent Pd/C / toluene / 6 h 2: 1.) AlCl3 / 1.) CH2Cl2, room temperature, 1 h, 2.) 3 h 3: 68 percent / NaBH4, BF3*OEt2 / tetrahydrofuran / 0.5 h 4: 66 percent / NEt3 / 3 h / Heating 5: 97 percent / 1N NaOH / dioxane; H2O / 0.5 h / Heating View Scheme