1: thien-3-yl bromide With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.666667 h; Inert atmosphere; 2: formic acid methyl ester in tetrahydrofuran; hexane 0.5 h; Inert atmosphere;

1: thien-3-yl bromide With n-butyllithium in diethyl ether; hexane T=-78°C; 0.5 h; 2: thiophene-3-carboxaldehyde in diethyl ether; hexane T=-78 - 20°C;

1: thien-3-yl bromide With n-butyllithium in tetrahydrofuran; hexane; dimethyl-ether T=-78 - -70°C; 0.25 h; 2: thiophene-2-carbaldehyde in tetrahydrofuran; hexane; dimethyl-ether T=-78 - -10°C; 3 h;

1: With n-butyllithium in tetrahydrofuran T=-78 - 20°C; 1 h; 2: With hydrogenchloride in tetrahydrofuran; water T=0°C;

hydrogenchloride 1.) THF, -70 deg C to 0 deg C, 1 h, 2.) 0 deg C; Yield given. Multistep reaction;

暂无反应条件数据

1: 77 percent / LiAlH4, AlCl3 2: 79 percent / N-bromosuccinimide / tetrahydrofuran / -5 °C 3: 40 percent / CuCl2, BuLi View Scheme

pyridinium chlorochromate in dichloromethane T=20°C; 2 h;

1.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 1.2: -78 - 20 °C 2.1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 3.1: copper / N,N-dimethyl-formamide / 15 h / Reflux View Scheme

1.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 1.2: -78 - 20 °C 2.1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 3.1: copper / N,N-dimethyl-formamide / 15 h / Reflux 4.1: hydrazine hydrate; potassium hydroxide / ethylene glycol / 8 h / 180 °C / Inert atmosphere 5.1: potassium iodide; potassium hydroxide / dimethyl sulfoxide / 16 h / 0 - 20 °C 6.1: N-bromosuccinmide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere; Darkness View Scheme