Multi-step reaction with 9 steps
1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -40 °C / Inert atmosphere
1.2: -40 - 20 °C / Inert atmosphere
2.1: sodium hydroxide / methanol; water / 1 h / 50 °C
2.2: Cooling
3.1: thionyl chloride / benzene / 3 h / Reflux; Inert atmosphere
4.1: palladium diacetate / diethyl ether / 3 h / 0 - 20 °C / Inert atmosphere
5.1: palladium 10% on activated carbon; hydrogen / ethanol / 2 h / 20 °C / 760.05 Torr
6.1: sodium tetrahydroborate / methanol / 2 h / 0 °C
6.2: Cooling
7.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C / Inert atmosphere
7.2: 8 h / 20 °C / Inert atmosphere
8.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / Inert atmosphere; Reflux
9.1: potassium carbonate; potassium iodide / acetone / Reflux; Inert atmosphere
With
sodium tetrahydroborate; n-butyllithium; thionyl chloride; 2,2'-azobis(isobutyronitrile); palladium 10% on activated carbon; hydrogen; tri-n-butyl-tin hydride; palladium diacetate; sodium hydride; potassium carbonate; diisopropylamine; potassium iodide; sodium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; water; acetone; toluene; mineral oil; benzene;
DOI:10.1016/j.tet.2012.05.041