1: thionyl chloride 2: 99 percent / sodium carbonate / H2O; diethyl ether / 4 h 3: 1.) TMEDA, sec-BuLi / 1.) ether, 0 deg C, 1 h; 2.) -78 deg C -> ambient temp. View Scheme

1: 81 percent / lithium diisopropylamide 2: 88 percent / potassium tert-butoxide, water / 2-methyl-propan-2-ol 3: thionyl chloride 4: 99 percent / sodium carbonate / H2O; diethyl ether / 4 h 5: 1.) TMEDA, sec-BuLi / 1.) ether, 0 deg C, 1 h; 2.) -78 deg C -> ambient temp. View Scheme

1: 88 percent / potassium tert-butoxide, water / 2-methyl-propan-2-ol 2: thionyl chloride 3: 99 percent / sodium carbonate / H2O; diethyl ether / 4 h 4: 1.) TMEDA, sec-BuLi / 1.) ether, 0 deg C, 1 h; 2.) -78 deg C -> ambient temp. View Scheme

N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium 1.) ether, 0 deg C, 1 h; 2.) -78 deg C -> ambient temp.; Yield given. Multistep reaction;

hydrogenchloride in water 72 h; Heating;