1: 69 percent / sodium bis(2-methoxyethoxy)aluminum hyride, morpholine / toluene / 4 h / -15 °C 2: 73 percent / sodium methylate / dimethylformamide / 0.25 h / 75 °C 3: 59 percent / propan-2-ol / 0.5 h / Heating 4: 73 percent / sodium methylate / ethanol / 40 h / Heating View Scheme

1: 69 percent / sodium bis(2-methoxyethoxy)aluminum hyride, morpholine / toluene / 4 h / -15 °C 2: 73 percent / sodium methylate / dimethylformamide / 0.25 h / 75 °C 3: 59 percent / propan-2-ol / 0.5 h / Heating 4: 73 percent / sodium methylate / ethanol / 40 h / Heating 5: 55 percent / phosphorus oxychloride / pyridine / 3 h / 20 - 30 °C View Scheme