1: 162 mg / LAH; aluminum chloride / tetrahydrofuran / 0 deg C, 30 min; reflux, 2 h 2: 69 percent / oxalyl chloride; dimethyl sulfoxide / CH2Cl2 / 0.33 h / -78 °C 3: 76 mg / ruthenium(III) chloride hydrate; NaIO4 / CCl4; acetonitrile; H2O / 6 h View Scheme

1.1: 162 mg / LAH; aluminum chloride / tetrahydrofuran / 0 deg C, 30 min; reflux, 2 h 2.1: 69 percent / oxalyl chloride; dimethyl sulfoxide / CH2Cl2 / 0.33 h / -78 °C 3.1: 76 mg / ruthenium(III) chloride hydrate; NaIO4 / CCl4; acetonitrile; H2O / 6 h 4.1: BBr3 / CH2Cl2 / 0.67 h / -78 - -40 °C 4.2: 50 percent / 37 percent hydrogen chloride / H2O / 1 h / Heating View Scheme

lithium aluminium tetrahydride; aluminium trichloride in tetrahydrofuran 0 deg C, 30 min; reflux, 2 h;