1: 1) n-butyllithium / 1) ether, -70 deg C, 6 h; 2) ether, -70 deg C, 12 h 2: Na / methanol / 6 h / 0 °C 3: 55.5 percent / N2 / various solvent(s) / 0.33 h / 110 °C 4: 93 percent / 1) KOH, H2O; 2) 5 N HCl / 1) reflux, 3.5 h; 2) 0 deg C View Scheme

1: 1) n-butyllithium / 1) ether, -70 deg C, 6 h; 2) ether, -70 deg C, 12 h 2: Na / methanol / 6 h / 0 °C 3: 55.5 percent / N2 / various solvent(s) / 0.33 h / 110 °C 4: 93 percent / 1) KOH, H2O; 2) 5 N HCl / 1) reflux, 3.5 h; 2) 0 deg C 5: 74 percent / CuO, Cr2O3 / quinoline / 7.5 h / 190 - 195 °C View Scheme