1: KOH / ethanol / 1.5 h / Heating 2: H2, HCl / Pd-C / ethanol View Scheme

hydrogen; palladium on activated charcoal in methanol

1: 1.) oxalyl chloride / 1.) benzene, reflux, 9 h, 2.) pyridine, N,N-dimethylaminopyridine, r.t., 48 h 2: 1.73 g / CH3COOH, H2 / 10percent Pd/C / ethyl acetate / 760 Torr 3: 840 mg / DMAP / pyridine / Ambient temperature 4: NBS / CCl4 / 1.5 h / Heating 5: acetonitrile / Heating; overnight 6: Et3N / toluene / 16 h / Heating 7: LiAlH4 / tetrahydrofuran / 8 h View Scheme

1: 1.73 g / CH3COOH, H2 / 10percent Pd/C / ethyl acetate / 760 Torr 2: 840 mg / DMAP / pyridine / Ambient temperature 3: NBS / CCl4 / 1.5 h / Heating 4: acetonitrile / Heating; overnight 5: Et3N / toluene / 16 h / Heating 6: LiAlH4 / tetrahydrofuran / 8 h View Scheme

1: 92 percent / Tl(NO3)3*3H2O / methanol 2: 65 percent / KOH / aq. ethanol / 2 h / Heating 3: 12 percent / H2 / Pd/C / methanol View Scheme

1: 65 percent / KOH / aq. ethanol / 2 h / Heating 2: 12 percent / H2 / Pd/C / methanol View Scheme

1: 840 mg / DMAP / pyridine / Ambient temperature 2: NBS / CCl4 / 1.5 h / Heating 3: acetonitrile / Heating; overnight 4: Et3N / toluene / 16 h / Heating 5: LiAlH4 / tetrahydrofuran / 8 h View Scheme

1: NBS / CCl4 / 1.5 h / Heating 2: acetonitrile / Heating; overnight 3: Et3N / toluene / 16 h / Heating 4: LiAlH4 / tetrahydrofuran / 8 h View Scheme

1: acetonitrile / Heating; overnight 2: Et3N / toluene / 16 h / Heating 3: LiAlH4 / tetrahydrofuran / 8 h View Scheme