hydrogen; palladium 10 on activated carbon in methanol 24 h;

lithium aluminium tetrahydride in tetrahydrofuran 6 h; Heating;

1: 65 percent / AlH3 / tetrahydrofuran / 0 °C 2: H2 / 10percent Pd/C / ethanol View Scheme

1: 78 percent / Lawesson's reagent / tetrahydrofuran / 20 °C 2: 95 percent / benzene / 12 h / 20 °C 3: 65 percent / Et3N / dimethylformamide / 24 h / 20 °C 4: 79 percent / HCO2NH4 / Pd-C / methanol / Heating 5: 77 percent / LAH / tetrahydrofuran / 6 h / Heating View Scheme

potassium carbonate in N,N-dimethyl-formamide T=60 - 65°C; 7 h;