1: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 2: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme

sulfuric acid; hydrogen; palladium on activated charcoal in ethyl acetate P=2942.03 Torr; 4 h; Ambient temperature; Yield given;

1: 91 percent / p-TsOH*H2O / toluene / 20 h / Heating 2: 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 3: 1.) PPh3, 2.) NBS / 1.) DMF, CH2Cl2, 25 deg C, 10 min, 2.) DMF, CH2Cl2, from -78 to 25 deg C, 2 h 4: 96 percent / dimethylsulfoxide / 1.5 h / 25 °C 5: 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 6: H2 / 10percent Pd/C View Scheme

chromium(VI) oxide in pyridine T=0°C; 2 h; Yield given;