1: 76 percent / acetic acid; dimethylformamide / 2 h / 80 °C 2: 1) 60percent sodium hydride / 1) DMF, 0 deg C, 0.5 h, 2) room temperature, 3 h 3: 100 percent / H2 / Raney Ni / acetic acid / 3 h 4: NaNO2, HOAc / acetic anhydride / 4 h / 0 °C 5: CCl4 / 5 h / Heating 6: 33.5 percent / 1 M H2SO4 / 1,2-dimethoxy-ethane / 24 h / 55 °C View Scheme

1: 76 percent / acetic acid; dimethylformamide / 2 h / 80 °C 2: 1) 60percent sodium hydride / 1) DMF, 0 deg C, 0.5 h, 2) room temperature, 3 h 3: 100 percent / H2 / Raney Ni / acetic acid / 3 h 4: NaNO2, HOAc / acetic anhydride / 4 h / 0 °C 5: CCl4 / 5 h / Heating 6: 33.5 percent / 1 M H2SO4 / 1,2-dimethoxy-ethane / 24 h / 55 °C 7: 69.5 percent / 2) p-TsOH / toluene / Heating; 1) 30 min, 2) 3 h View Scheme

1: Na2CO3 / dimethylformamide / 70 °C 2: NaH / dimethylformamide / Ambient temperature 4: 1.) LiOH; 2.) AcOH / 1.) EtOH, r.t.; 2.) r.t. 5: 80 percent / TFA / Ambient temperature 6: 73 percent / p-TsOH / toluene View Scheme

1: Na2CO3 / dimethylformamide / 70 °C 2: NaH / dimethylformamide / Ambient temperature 4: 1.) LiOH; 2.) AcOH / 1.) EtOH, r.t.; 2.) r.t. 5: 80 percent / TFA / Ambient temperature View Scheme

Multi-step reaction with 4 steps 1: Na2CO3 / dimethylformamide / 70 °C2: NaH / dimethylformamide / Ambient temperature4: 1.) LiOH; 2.) AcOH / 1.) EtOH, r.t.; 2.) r.t.  

Multi-step reaction with 3 steps 1: 93.2 percent / Na2CO3 / dimethylformamide / 1 h / 70 °C2: 56.4 percent / 1) sodium hydride / 1) DMF, room temperature, 1 h, 2) room temperature, 3 h3: 99.8 percent / H2 / Raney Ni / acetic acid / 3 h  

Multi-step reaction with 3 steps 1: Na2CO3 / dimethylformamide / 70 °C2: NaH / dimethylformamide / Ambient temperature  

Multi-step reaction with 2 steps 1: Na2CO3 / dimethylformamide / 70 °C2: NaH / dimethylformamide / Ambient temperature  

Multi-step reaction with 5 steps 1: 76 percent / acetic acid; dimethylformamide / 2 h / 80 °C2: 1) 60percent sodium hydride / 1) DMF, 0 deg C, 0.5 h, 2) room temperature, 3 h3: 100 percent / H2 / Raney Ni / acetic acid / 3 h4: NaNO2, HOAc / acetic anhydride / 4 h / 0 °C5: CCl4 / 5 h / Heating  

Multi-step reaction with 2 steps 1: 76 percent / acetic acid; dimethylformamide / 2 h / 80 °C2: 1) 60percent sodium hydride / 1) DMF, 0 deg C, 0.5 h, 2) room temperature, 3 h