1: CH2Cl2 / 14 h / Ambient temperature 2: 70 percent / thionyl chloride / benzene; CH2Cl2 / 1.) reflux, 2.) room temperature, 2.5 h 3: 2.) ethanol / 1.) pentane, -78 deg C, 2.) pentane, room temperature View Scheme

1: 70 percent / thionyl chloride / benzene; CH2Cl2 / 1.) reflux, 2.) room temperature, 2.5 h 2: 2.) ethanol / 1.) pentane, -78 deg C, 2.) pentane, room temperature View Scheme

1: thionyl chloride / 1 h / 100 °C 2: CH2Cl2 / 14 h / Ambient temperature 3: 70 percent / thionyl chloride / benzene; CH2Cl2 / 1.) reflux, 2.) room temperature, 2.5 h 4: 2.) ethanol / 1.) pentane, -78 deg C, 2.) pentane, room temperature View Scheme

ethanol 1.) pentane, -78 deg C, 2.) pentane, room temperature; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

N,N,N',N,-tetramethylethylenediamine 1) ether, -55 deg C, 0.08 h, 2) -55 deg C to rt; Yield given. Multistep reaction;