sodium hydride in N,N-dimethyl-formamide T=60°C; 2.5 h; Yield given;

1: toluene / 3 h / Heating 2: 5percent Pd/C / toluene / 1 h / Heating 3: thionyl chloride / CHCl3 / 0.33 h / Heating 4: NaH / dimethylformamide / 2.5 h / 60 °C View Scheme

1: H2 / 5percent Pd/C / toluene / 1 h / 760 Torr / Ambient temperature 2: toluene / 3 h / Heating 3: 5percent Pd/C / toluene / 1 h / Heating 4: thionyl chloride / CHCl3 / 0.33 h / Heating 5: NaH / dimethylformamide / 2.5 h / 60 °C View Scheme

1: 79 percent / H2O / 4 h / 25 °C 2: H2 / 5percent Pd/C / toluene / 1 h / 760 Torr / Ambient temperature 3: toluene / 3 h / Heating 4: 5percent Pd/C / toluene / 1 h / Heating 5: thionyl chloride / CHCl3 / 0.33 h / Heating 6: NaH / dimethylformamide / 2.5 h / 60 °C View Scheme

1: thionyl chloride / CHCl3 / 0.33 h / Heating 2: NaH / dimethylformamide / 2.5 h / 60 °C View Scheme