hydrogen; palladium on activated charcoal in methanol T=20°C; 20 h;

1: 1.) NaBH4, BF3*Et2O, 2.) NaOH, H2O2 / 1.) diglyme, a) 25 deg C, 1 h, b) 160 - 165 deg C, 2.5 h, 2.) diglyme, water, RT, 1.5 h 2: 1.) PPh3, 2.) NBS / 1.) DMF, CH2Cl2, 25 deg C, 10 min, 2.) DMF, CH2Cl2, from -78 to 25 deg C, 2 h 3: 96 percent / dimethylsulfoxide / 1.5 h / 25 °C 4: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, from -40 to -30 deg C, 1.5 h, 2.) THF, hexane, 25 deg C, 22 h 5: H2 / 10percent Pd/C View Scheme