1: 82 percent / aq. NaBH4 / methanol / 2 h / Heating 2: 80 percent / pyridine / 3 h / Ambient temperature 3: 1.) NaH / 1.) DMF, 2.) DMF, 90 deg C, 2 h View Scheme

sodium tetrahydroborate in methanol 2 h; Heating;

sodium hydroxide in methanol; water 3 h;

1: NaBH4 / methanol / Heating 2: DEAD, PH3P / tetrahydrofuran / Ambient temperature View Scheme

1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / |Reflux; |Inert atmosphere 2: zinc / methanol; acetic acid / 1.08 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C View Scheme

1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / |Reflux; |Inert atmosphere 2: zinc / methanol; acetic acid / 1.08 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C 4: sodium hydroxide / methanol; water / 0.75 h / |Reflux View Scheme