aluminum oxide; pyridinium chlorochromate in toluene 2 h;

1: 1.) 2N H2SO4, NaNO2, 2.) H2O / 1.) 0 deg C, 2.) heating 2: 88 percent / pyridine / 24 h 3: 61 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4: 58 percent / p-TosOH / toluene / 0.75 h 5: 83 percent / pyridinium chlorochromate, Al2O3 / toluene / 2 h View Scheme

1: 88 percent / pyridine / 24 h 2: 61 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 58 percent / p-TosOH / toluene / 0.75 h 4: 83 percent / pyridinium chlorochromate, Al2O3 / toluene / 2 h View Scheme

1: 61 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 58 percent / p-TosOH / toluene / 0.75 h 3: 83 percent / pyridinium chlorochromate, Al2O3 / toluene / 2 h View Scheme

1: 58 percent / p-TosOH / toluene / 0.75 h 2: 83 percent / pyridinium chlorochromate, Al2O3 / toluene / 2 h View Scheme