pyridinium p-toluenesulfonate; magnesium sulfate in dichloromethane 2 h; Ambient temperature;

1: 88 percent / Sulfuryl chloride / toluene; diethyl ether / 2 h / 0 °C 2: 78 percent / 29 percent NH4OH/H2O / CH2Cl2 / 0 °C 3: 99 percent / Pyridinium p-toluenesulfonate, (PPTS)/anhydr. MgSO4 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 78 percent / 29 percent NH4OH/H2O / CH2Cl2 / 0 °C 2: 99 percent / Pyridinium p-toluenesulfonate, (PPTS)/anhydr. MgSO4 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to 25 deg C, 20 h 2: 81 percent / trimethylsilyl iodide / CH2Cl2 / 7 h / 25 °C View Scheme

sodium cyanoborohydride; trifluoroacetic acid in tetrahydrofuran Ambient temperaturepH 4-5, indicator Bromocresol Green or pH 5-6, indicator Chlorophenol Red;