1: 63 percent / potassium iodide / ethanol; H2O / 72 h / Heating 2: 1) lithium diisopropylamide / 1) THF, hexane, -50 deg C, 20 min, 2) THF, -50 deg C, 30 min View Scheme

p-toluenesulfonic acid monohydrate in methanol 6 h; Ambient temperature;

1: 1.) 1.6 M butyllithium / 1.) hexane, THF, a.) -15 to -17 deg C, 30 min, b.) RT, 1 h, 2.) RT, 10 h 2: p-toluenesulfonic acid / 5 h / 110 - 130 °C / 170 - 200 Torr 3: hydrochloric acid / H2O / 25 °C / var. -log<H+> values of the solution View Scheme