n-butyllithium; sodium hydride 1.) THF, HMPA, -12 - 0 deg C -> 25 deg C; 25 deg C, 20 min, 2.) THF, HMPA, hexane, -15 - 0 deg C -> 25 deg C, 25 deg C, 0.5 h, 3.) -15 - 4 deg C, 30 min, RT, 3 h;

1: 80 percent / KOH / methanol; H2O / 10 h / Heating 2: 75 percent / PCC / CH2Cl2 / 6 h / Ambient temperature 3: 70 percent / NaOH / aq. ethanol / 6 h / Heating View Scheme

1: 80 percent / KOH / methanol; H2O / 10 h / Heating 2: 75 percent / PCC / CH2Cl2 / 6 h / Ambient temperature View Scheme