1: 1.) 1-butyllithium / 1.) tetrahydrofuran/hexane, -78 deg C, 10 min, -20 deg C, 2 h; 2.) tetrahydrofuran/hexane, -78 deg C, 1 h 2: 80percent aq. acetic acid / methanol / 0.17 h / Heating View Scheme

1: 1.) 1-butyllithium / 1.) tetrahydrofuran/hexane, -78 deg C, 10 min, -20 deg C, 2 h; 2.) tetrahydrofuran/hexane, -78 deg C, 1 h 2: 100 percent / pyridine / 12 h / 0 °C 3: 45 percent / 80percent aq. acetic acid / 65 h 4: 100 percent / sodium / methanol / 1 h / Ambient temperature View Scheme

1: 1.) 1-butyllithium / 1.) tetrahydrofuran/hexane, -78 deg C, 10 min, -20 deg C, 2 h; 2.) tetrahydrofuran/hexane, -78 deg C, 1 h 2: 90 percent / 80percent aq. acetic acid / 10 h / Heating View Scheme