Multi-step reaction with 10 steps
1.1: tetrahydrofuran / -78 - 20 °C / Inert atmosphere
2.1: 1H-imidazole; sodium hydride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
2.2: 1 h / 20 °C / Inert atmosphere
3.1: tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
4.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 24 h / Reflux; Inert atmosphere
5.1: hydrogenchloride / ethanol; water / 3 h / Reflux; Inert atmosphere
6.1: pyridine / ethanol / 24 h / 20 °C / Inert atmosphere
7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 3 h / 45 °C / Inert atmosphere
8.1: tetrabutylammomium bromide; palladium diacetate; sodium hydrogencarbonate / N,N-dimethyl-formamide / 8 h / 85 °C / Inert atmosphere
9.1: sodium methylate / methanol / 20 °C
10.1: water; lithium hydroxide / tetrahydrofuran; methanol; water / 3 h / 20 °C / Inert atmosphere
With
pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; 2,2'-azobis(isobutyronitrile); tetrabutylammomium bromide; water; tri-n-butyl-tin hydride; sodium methylate; palladium diacetate; sodium hydride; sodium hydrogencarbonate; lithium hydroxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
8.1: Heck coupling / 9.1: Zemplen reaction;
DOI:10.1002/chem.201003402