Multi-step reaction with 12 steps
1: thionyl chloride / 5 h / 0 °C / Reflux
2: potassium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; ethyl acetate
3: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
4: triphenylphosphine; tetrachloromethane / tetrahydrofuran / 2 h / Inert atmosphere; Reflux
5: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 20 °C / Inert atmosphere
6: palladium 10% on activated carbon; hydrogen / methanol
7: pyridine / dichloromethane / 2 h / 0 °C
8: potassium carbonate / methanol; dichloromethane / 12 h / Inert atmosphere; Reflux
9: palladium 10% on activated carbon; hydrogen / ethanol / 16 h / 3102.97 Torr
10: dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
11: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C
12: lithium hydroxide monohydrate; water / tetrahydrofuran / 24 h / 20 °C
With
pyridine; tetrachloromethane; bis-triphenylphosphine-palladium(II) chloride; lithium aluminium tetrahydride; thionyl chloride; lithium hydroxide monohydrate; palladium 10% on activated carbon; water; hydrogen; tetra-(n-butyl)ammonium iodide; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;