in tetrahydrofuran; diethyl ether T=-40°C; 2 h;

in tetrahydrofuran T=-78 - 0°C;

1: With diisobutylaluminium hydride in tetrahydrofuran; hexane T=-78°C; 1.5 h; Inert atmosphere; 2: With ammonia; iodine in tetrahydrofuran; hexane; water T=0 - 20°C; Inert atmosphere;

in tetrahydrofuran T=0°C;

1: Methyltriphenylphosphonium bromide With n-butyllithium in tetrahydrofuran; hexane T=-15°C; 2: N-methoxy-N-methyl-(E)-3-phenyl-2-propenamide in tetrahydrofuran; hexane T=-78 - 20°C; Wittig reaction; 3: With hydrogenchloride in tetrahydrofuran; diethyl ether; hexane T=20°C;

cerium(III) chloride in tetrahydrofuran T=-78°C; 3 h;

lithium aluminium tetrahydride in tetrahydrofuran

Schwartz's reagent in tetrahydrofuran T=20°C; 0.333333 h;

1: 2-methyl-but-3-yn-2-ol With n-butyllithium in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane T=-78°C; 0.5 h; Inert atmosphere; 2: N-methoxy-N-methyl-(E)-3-phenyl-2-propenamide in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane T=-78 - 20°C; 3: With water; ammonium chloride in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane

1.1: cesium fluoride / toluene / 0.17 h / 0 °C 1.2: 24 h / 0 - 20 °C 2.1: tetrabutyl ammonium fluoride; water / toluene; tetrahydrofuran / 2 h / 20 °C View Scheme