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: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 20 °C
8.1: hydrogen / palladium on activated charcoal / methanol / 12 h / 20 °C
9.1: diethylamino-sulfur trifluoride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
9.2: pH 8 - 9
10.1: phenyltrimethylammonium tribromide / chloroform / 0.5 h / Reflux
With
oxalyl dichloride; diethylamino-sulfur trifluoride; hydrogen; phenyltrimethylammonium tribromide; magnesium; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrakis(triphenylphosphine) palladium(0); palladium on activated charcoal; N,N-dimethyl-formamide;
In
tetrahydrofuran; methanol; dichloromethane; chloroform; toluene;