pyridinium chlorochromate in dichloromethane 3 h; Ambient temperature;

silica gel; pyridinium chlorochromate in dichloromethane 0.0333333 h; microwave irradiation;

1: 100 percent / LiAlH4 / diethyl ether / 2.5 h 2: 100 percent Chromat. / PCC / CH2Cl2 / 24 h View Scheme

1: 38 percent / conc. hydrochloric acid / 12 h / 170 °C 2: 81 percent / diborane / tetrahydrofuran / 3 h / -10 °C 3: 92.3 percent / diethyl ether / 2 h / Heating 4: p-toluenesulfonic acid / benzene / 16.5 h / Heating 5: H2 / 10percent palladium-on-carbon / ethanol / 5 h / Ambient temperature 6: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 92.3 percent / diethyl ether / 2 h / Heating 2: p-toluenesulfonic acid / benzene / 16.5 h / Heating 3: H2 / 10percent palladium-on-carbon / ethanol / 5 h / Ambient temperature 4: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 81 percent / diborane / tetrahydrofuran / 3 h / -10 °C 2: 92.3 percent / diethyl ether / 2 h / Heating 3: p-toluenesulfonic acid / benzene / 16.5 h / Heating 4: H2 / 10percent palladium-on-carbon / ethanol / 5 h / Ambient temperature 5: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: p-toluenesulfonic acid / benzene / 16.5 h / Heating 2: H2 / 10percent palladium-on-carbon / ethanol / 5 h / Ambient temperature 3: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: H2 / 10percent palladium-on-carbon / ethanol / 5 h / Ambient temperature 2: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Me3N / 1.) CH2Cl2, -78 deg C, 25 min, 2.) 15 min 2: 76 percent / tetrahydrofuran / 0.5 h / 0 °C 3: 95 percent / i-Pr2NEt / CH2Cl2 / 1 h / 0 °C 4: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / 80 °C 5: 98 percent / pyridinium p-toluene sulfonate / ethanol / 8 h / 60 °C 6: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Me3N / 1.) CH2Cl2, -78 deg C, 25 min, 2.) 1 h View Scheme

1: 76 percent / tetrahydrofuran / 0.5 h / 0 °C 2: 95 percent / i-Pr2NEt / CH2Cl2 / 1 h / 0 °C 3: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / 80 °C 4: 98 percent / pyridinium p-toluene sulfonate / ethanol / 8 h / 60 °C 5: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Me3N / 1.) CH2Cl2, -78 deg C, 25 min, 2.) 1 h View Scheme