aluminum oxide in diethyl ether T=20°C; 12 h;

toluene-4-sulfonic acid in benzene T=50°C; 12 h;

pyridinium chlorochromate in dichloromethane T=20°C; 4 h;

1.1: anhydrous sodium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 8 h / 20 °C 1.2: 220 mg / sulfuric acid / H2O; diethyl ether / 6 h / 20 °C 2.1: pyridine / diethyl ether / 0 - 20 °C 3.1: 84 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 20 °C View Scheme

1.1: isopropenyl acetate; p-toluenesulfonic acid monohydrate / 24 h / Heating 1.2: NaBH4 / aq. ethanol / 1.5 h / Heating 2.1: 96 percent / sodium hydride / dimethylformamide / 0 - 20 °C 3.1: anhydrous sodium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 8 h / 20 °C 3.2: 220 mg / sulfuric acid / H2O; diethyl ether / 6 h / 20 °C 4.1: pyridine / diethyl ether / 0 - 20 °C 5.1: 84 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 20 °C View Scheme

1.1: 96 percent / sodium hydride / dimethylformamide / 0 - 20 °C 2.1: anhydrous sodium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 8 h / 20 °C 2.2: 220 mg / sulfuric acid / H2O; diethyl ether / 6 h / 20 °C 3.1: pyridine / diethyl ether / 0 - 20 °C 4.1: 84 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 20 °C View Scheme

1: pyridine / diethyl ether / 0 - 20 °C 2: 84 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 20 °C View Scheme

1: 100 percent / LiAlH4 / diethyl ether / 0 - 20 °C 2: pyridine / diethyl ether / 0 - 20 °C 3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 20 °C View Scheme

1: sodium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 7 h / 20 °C 2: 551 mg / active neutral alumina / diethyl ether / 12 h / 20 °C 3: 100 percent / LiAlH4 / diethyl ether / 0 - 20 °C 4: pyridine / diethyl ether / 0 - 20 °C 5: 84 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 20 °C View Scheme