potassium hydroxide in methanol 22 h; Heating;

chloro-trimethyl-silane; sodium iodide in acetonitrile Ambient temperature;

1: 1.) n-BuLi / 1.) THF, hexane, -78 to -20 deg C, 1 h, 2.) THF, a) -20 deg C, 30 min, b) -20 deg C to room temperature, 30 min, c) room temperature, 4 h 2: 53 percent / Me3SiCl, NaI / acetonitrile / Ambient temperature View Scheme

1: 1.) n-BuLi, 2.) toluene-p-sulphonyl azide, 3.) tetrasodium pyrophosphate 2: 90 percent / chlorobenzene / 0.42 h / Heating View Scheme

1: 1.) n-BuLi, 3.) p-TsOH 2: 1.) n-BuLi, 2.) toluene-p-sulphonyl azide, 3.) tetrasodium pyrophosphate 3: 90 percent / chlorobenzene / 0.42 h / Heating View Scheme