1: 1.) n-BuLi / 1.) THF, -78 deg C 2: 1.) n-BuLi, 2.) dry O2 / 1.) THF, -78 deg C, 2.) THF, -78 deg C, 10 min 3: 90 percent / H2O, TsOH / tetrahydrofuran 4: 78 percent / NaOH / ethanol View Scheme

hydrogenchloride; natronlauge; lithium diisopropyl amide Yield given. Multistep reaction;

1: 67.6 percent / benzene / 4 h / Heating 2: n-BuLi, HMPTA / tetrahydrofuran / 3 h / -78 °C 3: p-Toluenesulfonic acid / acetone View Scheme

lithium diisopropyl amide 1.) THF, -78 deg C, 2.) -78 deg C, 30 min, 3.) -78 -> 0 deg C, 2h; Yield given. Multistep reaction;

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