1.1: thionyl chloride; triethylamine / CH2Cl2 / 0.5 h / 0 °C 2.1: sodium periodate; ruthenium(III) chloride trihydrate / CCl4; acetonitrile; H2O / 20 °C 3.1: tetrabutylammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / Heating 3.2: 381 mg / hydrochloric acid / toluene / 2 h / 20 °C 4.1: 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: sodium periodate; ruthenium(III) chloride trihydrate / CCl4; acetonitrile; H2O / 20 °C 3.1: tetrabutylammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / Heating 3.2: 381 mg / hydrochloric acid / toluene / 2 h / 20 °C View Scheme