Multi-step reaction with 10 steps
1.1: pyridine; 20% palladium hydroxide on carbon; hydrogen / methanol; ethyl acetate / 2 h
2.1: N-Bromosuccinimide / dichloromethane / 4 h / -78 - 20 °C / Inert atmosphere
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.42 h / 0 - 20 °C / Inert atmosphere
4.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0 h / -78 °C / Inert atmosphere
4.2: -78 - 20 °C / Inert atmosphere
4.3: 20 °C / Inert atmosphere
5.1: barium manganate / benzene / 3.5 h / 20 °C / Inert atmosphere
6.1: ethanol / 3 h / 20 °C / Inert atmosphere
7.1: lithium tetrafluoroborate; water / acetonitrile / 0.25 h / 82 °C / Inert atmosphere; Microwave irradiation
8.1: calcium sulfate; scandium tris(trifluoromethanesulfonate) / 1,2-dichloro-ethane / 67.5 h / -30 - 0 °C / Inert atmosphere
9.1: pyridine; dmap / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
10.1: boron tribromide / dichloromethane / 0.08 h / -90 °C / Inert atmosphere
10.2: -90 - 20 °C / Inert atmosphere
With
pyridine; dmap; calcium sulfate; N-Bromosuccinimide; lithium tetrafluoroborate; barium manganate; 20% palladium hydroxide on carbon; water; hydrogen; tert.-butyl lithium; boron tribromide; sodium hydride; scandium tris(trifluoromethanesulfonate);
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; acetonitrile; mineral oil; pentane; benzene;
DOI:10.1016/j.tet.2011.05.117