1: 1.) NaH / 1.) benzene, reflux, 2 h, 2.) benzene, reflux, overnight 2: 56 percent / pyridine / Ambient temperature 3: 100 percent / CoCl2, NaBH4 / tetrahydrofuran; ethanol / 1.) 0 deg C, 10 min, 2.) RT, overnight 4: 99 percent / ceric ammonium nitrate / H2O; acetonitrile / 0.5 h / Ambient temperature View Scheme

1: 1.) NaH / 1.) benzene, reflux, 2 h, 2.) benzene, reflux, overnight 2: 56 percent / pyridine / Ambient temperature 3: 100 percent / CoCl2, NaBH4 / tetrahydrofuran; ethanol / 1.) 0 deg C, 10 min, 2.) RT, overnight 4: 96 percent / aq. NaOH / methanol / Ambient temperature 5: 85 percent / PBr3 / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) RT, overnight 6: 83 percent / Ce(NH4)2(NO3)6 / acetonitrile; H2O View Scheme