Multi-step reaction with 10 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 6 h / Reflux
2.1: sodium hydroxide / methanol / 2 h / Reflux
2.2: pH 2 - 3
3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
4.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
5.1: magnesium / tetrahydrofuran / 60 - 70 °C / Inert atmosphere
5.2: -78 - 20 °C / Inert atmosphere
6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 18 h / Inert atmosphere; Reflux
7.1: hydrogen / palladium on activated charcoal / methanol / 2 h / 20 °C / 760.05 Torr
8.1: phenyltrimethylammonium tribromide / chloroform / 0.5 h / Reflux
9.1: ethanol / 2 h / Reflux
10.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 4 h / Inert atmosphere; Reflux
With
oxalyl dichloride; hydrogen; phenyltrimethylammonium tribromide; caesium carbonate; magnesium; triethylamine; sodium hydroxide;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tris-(dibenzylideneacetone)dipalladium(0); tetrakis(triphenylphosphine) palladium(0); palladium on activated charcoal; N,N-dimethyl-formamide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; toluene;