1: propargyl alcohol With n-butyl-magnesium chloride in tetrahydrofuran 1.33333 h; cooling; 2: With cerium(III) chloride in tetrahydrofuran T=0°C; 1.5 h; 3: 2,2-Dimethyl-1,3-dioxan-5-one in tetrahydrofuran T=0°C; 1.5 h;

quinoline; hydrogen; Pd-BaSO4 in ethanol T=20°C; 7 h;

1: 91 percent / quinoline; H2 / Pd/BaSO4 / ethanol / 7 h / 20 °C 2: imidazole / CH2Cl2 / 1 h / 20 °C 3: 2.41 g / m-chloroperbenzoic acid / CH2Cl2 / 20 °C 4: 99 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 5: 94 percent / PPh3; DEAD / toluene; tetrahydrofuran / 1.5 h / 20 °C 6: 95 percent / sodium methoxide / methanol / 1 h / Heating 7: 83 percent / PPh3; DEAD / tetrahydrofuran / 1 h / 20 °C 8: 90 percent / ammonia / methanol / 80 °C 9: 87 percent / tributyltin hydride; AIBN / toluene / 10 h / Heating View Scheme