Multi-step reaction with 10 steps
1.1: pyridine / 0 - 20 °C / Inert atmosphere
2.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C / Inert atmosphere
3.1: potassium permanganate; magnesium sulfate / water / 1.5 h / 80 °C / Inert atmosphere
4.1: potassium carbonate / N,N-dimethyl-formamide / 70 °C / Inert atmosphere
5.1: 5%-palladium/activated carbon; hydrogen / methanol; dichloromethane / 20 h
6.1: thionyl chloride / 1 h / Inert atmosphere; Reflux
6.2: 18 h / Inert atmosphere; Reflux
7.1: dmap / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
8.1: 5%-palladium/activated carbon; hydrogen / methanol; dichloromethane / 20 h
9.1: thionyl chloride / 1 h / Inert atmosphere; Reflux
9.2: 18 h / Inert atmosphere; Reflux
10.1: dmap / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
With
pyridine; dmap; potassium permanganate; thionyl chloride; 5%-palladium/activated carbon; hydrogen; magnesium sulfate; potassium carbonate; trifluoroacetic acid; sodium nitrite;
In
methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2011.11.010