1.1: thionyl chloride; triethylamine / CH2Cl2 / 0.5 h / 0 °C 2.1: 1.09 g / sodium periodate; ruthenium(III) chloride trihydrate / CCl4; acetonitrile; H2O / 2 h / 20 °C 3.1: tetrabutylammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / Heating 3.2: 87 percent / sulfuric acid / toluene; tetrahydrofuran; H2O / 1 h / 20 °C 4.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 5.1: 87 percent / sodium borohydride / propan-2-ol / 24 h / Heating View Scheme

1.1: thionyl chloride; triethylamine / CH2Cl2 / 0.5 h / 0 °C 2.1: 1.09 g / sodium periodate; ruthenium(III) chloride trihydrate / CCl4; acetonitrile; H2O / 2 h / 20 °C 3.1: tetrabutylammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / Heating 3.2: 87 percent / sulfuric acid / toluene; tetrahydrofuran; H2O / 1 h / 20 °C 4.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme