lithium aluminium tetrahydride in tetrahydrofuran 1 h; Ambient temperature;

ammonium chloride; lithium diisopropyl amide 1.) Et2O, hexane, -78 deg C, 30 min; 2.) Et2O, hexane; Yield given. Multistep reaction. Yields of byproduct given;

4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane T=-23°C; 24 h;

1.1: tetrahydrofuran; diethyl ether / 1 h / 0 °C 2.1: O3 / methanol / -78 °C 2.2: 84 percent / NaBH4 / methanol / 0.5 h / 0 °C View Scheme

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;

1.1: n-butylmagnesium chloride / tetrahydrofuran / 1.33 h / cooling 1.2: anhydrous cerium (III) chloride / tetrahydrofuran / 1.5 h / 0 °C 1.3: 84 percent / tetrahydrofuran / 1.5 h / 0 °C 2.1: 91 percent / quinoline; H2 / Pd/BaSO4 / ethanol / 7 h / 20 °C View Scheme

1.1: n-butylmagnesium chloride / tetrahydrofuran / 1.33 h / cooling 1.2: anhydrous cerium (III) chloride / tetrahydrofuran / 1.5 h / 0 °C 1.3: 84 percent / tetrahydrofuran / 1.5 h / 0 °C 2.1: 91 percent / quinoline; H2 / Pd/BaSO4 / ethanol / 7 h / 20 °C 3.1: imidazole / CH2Cl2 / 1 h / 20 °C 4.1: 2.41 g / m-chloroperbenzoic acid / CH2Cl2 / 20 °C 5.1: 99 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 94 percent / PPh3; DEAD / toluene; tetrahydrofuran / 1.5 h / 20 °C 7.1: 95 percent / sodium methoxide / methanol / 1 h / Heating 8.1: 83 percent / PPh3; DEAD / tetrahydrofuran / 1 h / 20 °C 9.1: 90 percent / ammonia / methanol / 80 °C 10.1: 87 percent / tributyltin hydride; AIBN / toluene / 10 h / Heating View Scheme

1: vinyl-magnesium chloride With zinc(II) chloride in tetrahydrofuran; tert-butyl methyl ether T=-5 - 0°C; 1.25 h; 2: 2,2-Dimethyl-1,3-dioxan-5-one in tetrahydrofuran; tert-butyl methyl ether T=-10 - -5°C; 2.5 h;

in tetrahydrofuran T=0°C; 0.5 h;