lithium aluminium tetrahydride in diethyl ether 0.5 h; Heating;

in N,N-dimethyl-aniline T=200°C; 4 h; Inert atmosphere;

1: potassium carbonate; sodium iodide / acetone / 72 h / 70 °C / |Inert atmosphere 2: N,N-dimethyl-aniline / 4 h / 200 °C / |Inert atmosphere View Scheme

1: 96 percent / N,N-diethylaniline / 1.25 h / 210 - 220 °C 2: 98 percent / LiAlH4 / diethyl ether / 0.5 h / Heating View Scheme

1: 79 percent / KI; K2CO3 / acetone / 48 h / 49 - 53 °C 2: 96 percent / N,N-diethylaniline / 1.25 h / 210 - 220 °C 3: 98 percent / LiAlH4 / diethyl ether / 0.5 h / Heating View Scheme

1: palladium diacetate; potassium carbonate / ethyl acetate / 0.83 h / 150 °C / 12929 Torr / Microwave irradiation; Molecular sieve 2: lithium aluminium tetrahydride / diethyl ether / 2 h / -15 °C / Inert atmosphere View Scheme

1: sulfuric acid / 12 h / Reflux 2: potassium carbonate / 1,4-dioxane / 72 h / 105 °C 3: palladium diacetate; potassium carbonate / ethyl acetate / 0.83 h / 150 °C / 12929 Torr / Microwave irradiation; Molecular sieve 4: lithium aluminium tetrahydride / diethyl ether / 2 h / -15 °C / Inert atmosphere View Scheme