sodium ethanolate 40 h; Heating;

sodium t-butanolate in tert-butyl alcohol 72 h; Heating;

sodium isopropanolate in isopropyl alcohol 40 h; Heating;

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -78 deg C, 0.5 h, b) RT, 0.5 h 2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, RT 3: conc. hydrochloric acid / aq. ethanol / 0.5 h / Ambient temperature 4: p-toluenesulfonic acid / 22 h / 156 °C View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -78 deg C, 0.5 h, b) RT, 0.5 h 2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, RT 3: conc. hydrochloric acid / aq. ethanol / 0.5 h / Ambient temperature 4: 63 percent / p-toluenesulfonic acid / acetic acid / 24 h / Heating View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -78 deg C, 0.5 h, b) RT, 0.5 h 2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, RT 3: conc. hydrochloric acid / aq. ethanol / 0.5 h / Ambient temperature 4: 37 percent / p-toluenesulfonic acid, acetic acid / 24 h / Heating View Scheme

sodium isopropanolate in isopropyl alcohol 40 h; Heating;

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -78 deg C, 0.5 h, b) RT, 0.5 h 2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, RT 3: conc. hydrochloric acid / aq. ethanol / 0.5 h / Ambient temperature 4: 32 percent / p-toluenesulfonic acid, acetic acid / 24 h / Heating View Scheme