1: 49 percent / Al2(SO4)3 / octane / 78 °C 2: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Me3N / 1.) CH2Cl2, -78 deg C, 25 min, 2.) 15 min 3: 76 percent / tetrahydrofuran / 0.5 h / 0 °C 4: 95 percent / i-Pr2NEt / CH2Cl2 / 1 h / 0 °C 5: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / 80 °C 6: 98 percent / pyridinium p-toluene sulfonate / ethanol / 8 h / 60 °C 7: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Me3N / 1.) CH2Cl2, -78 deg C, 25 min, 2.) 1 h View Scheme

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

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

1: 1.) Hg(OAc)2, 2.) NaBH4 / 1.) THF, H2O 2: 90 percent / pyridine / Ambient temperature 3: 77 percent / diethyl ether / 1.) -40 deg C, 3 h, 2.) room temperature, overnight 4: 82 percent / LiAlH4 / diethyl ether / 3 h / Heating 5: 72 percent / PCC / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: 90 percent / pyridine / Ambient temperature 2: 77 percent / diethyl ether / 1.) -40 deg C, 3 h, 2.) room temperature, overnight 3: 82 percent / LiAlH4 / diethyl ether / 3 h / Heating 4: 72 percent / PCC / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: 77 percent / diethyl ether / 1.) -40 deg C, 3 h, 2.) room temperature, overnight 2: 82 percent / LiAlH4 / diethyl ether / 3 h / Heating 3: 72 percent / PCC / CH2Cl2 / 3 h / Ambient temperature View Scheme