18-crown-6 ether in acetonitrile 20 h; Heating;

1: 27 percent / sec-butyllithium / tetrahydrofuran; cyclohexane / 3 h / -75 °C 2: 89 percent / potassium hydroxide / diethyl ether; H2O / 15 h / 25 °C 3: 71 percent / 18-crown-6 / acetonitrile / 20 h / Heating View Scheme

1: 95 percent / sodium borohydride / methanol / 0.25 h / 0 °C 2: 89 percent / potassium hydroxide / diethyl ether; H2O / 15 h / 25 °C 3: 71 percent / 18-crown-6 / acetonitrile / 20 h / Heating View Scheme

1: 89 percent / potassium hydroxide / diethyl ether; H2O / 15 h / 25 °C 2: 71 percent / 18-crown-6 / acetonitrile / 20 h / Heating View Scheme

1: 65 percent / bromine / CCl4 2: 43 percent / aq. ethanol / 6 h / Heating View Scheme

in ethanol 6 h; Heating;