thionyl chloride Heating;

1: 78 percent / LiAlH4 2: 79 percent / CrO3 / acetone; aq. H2SO4 / 14 h / Ambient temperature 3: 92 percent / Cl2OS / Heating View Scheme

1: H2, quinoline / Pd (10percent on BaSO4) / methanol / 7 h / Ambient temperature 2: oxalyl chloride / CH2Cl2 / 2 h / 0 °C View Scheme

1: 1.) methylmagnesium bromide / 1.) THF, Et2O, rt, 2h 2.) a) -23 deg C, 30 min b) rt, 2 h 2: H2, quinoline / Pd (10percent on BaSO4) / methanol / 7 h / Ambient temperature 3: oxalyl chloride / CH2Cl2 / 2 h / 0 °C View Scheme

1: 79 percent / CrO3 / acetone; aq. H2SO4 / 14 h / Ambient temperature 2: 92 percent / Cl2OS / Heating View Scheme