n-butyllithium; p-toluenesulfonyl chloride 1.) THF, -78 deg -> 0 deg C, 2.) -78 deg C -> room temperature; Yield given. Multistep reaction;

1: 1) n-BuLi / 1) DME, 25 deg C, 2) -78 deg C, then 25 deg C 2: n-BuLi / tetrahydrofuran / 1) -78 deg C, 2) 25 deg C, 10 min 3: NaH / tetrahydrofuran / 25 °C View Scheme

1: 50 percent / triethylamine / diethyl ether / -78 °C 3: 1.) n-butyl-lithium / 1.) DME, -78 deg C -> room temperature, 60 min, room temperature 30 min, 2.) -78 deg C -> room temperature 15 min 4: 1.) n-butyl-lithium, 2.) toluene-4-sulphonyl chloride / 1.) THF, -78 deg -> 0 deg C, 2.) -78 deg C -> room temperature View Scheme

2: 1.) n-butyl-lithium / 1.) DME, -78 deg C -> room temperature, 60 min, room temperature 30 min, 2.) -78 deg C -> room temperature 15 min 3: 1.) n-butyl-lithium, 2.) toluene-4-sulphonyl chloride / 1.) THF, -78 deg -> 0 deg C, 2.) -78 deg C -> room temperature View Scheme