pyridinium chlorochromate in dichloromethane 3.5 h; Ambient temperature;

1: lithium aluminum hydride / diethyl ether / 1.) 0 deg C, 0.5 h, 2.) 25 deg C, 5 h 2: chromium trioxide, pyridine / CH2Cl2 / 0.17 h / 25 °C View Scheme

1: 59 percent / NaH / dimethylformamide / 2 h / Ambient temperature 2: 88 percent / pyridinium chlorochromate / CH2Cl2 / 3.5 h / Ambient temperature View Scheme

1: 89 percent / hydrogen / 10percent palladium-carbon / acetic acid 2: 4.08 g / potassium carbonate / acetone / 0.5 h / Heating 3: 51 percent / pyridinium chlorochromate / CH2Cl2 View Scheme

1: 85 percent / lithium aluminium hydride / diethyl ether / 2.5 h / Heating 2: 89 percent / hydrogen / 10percent palladium-carbon / acetic acid 3: 4.08 g / potassium carbonate / acetone / 0.5 h / Heating 4: 51 percent / pyridinium chlorochromate / CH2Cl2 View Scheme

1: 88 percent / LiAlH4 / tetrahydrofuran / 2 h / 60 °C 2: 59 percent / NaH / dimethylformamide / 2 h / Ambient temperature 3: 88 percent / pyridinium chlorochromate / CH2Cl2 / 3.5 h / Ambient temperature View Scheme