Multi-step reaction with 13 steps
1.1: aluminum (III) chloride / 1,1,2,2-tetrachloroethane
2.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C
2.2: 120 - 215 °C
3.1: methanesulfonic acid / 0.5 h / 90 °C / Inert atmosphere
4.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C
4.2: 120 - 215 °C
5.1: aluminum (III) chloride / 1,1,2,2-tetrachloroethane / 20 °C / Cooling with ice
6.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C
6.2: 120 - 215 °C
7.1: sulfuric acid / Reflux
8.1: palladium 10% on activated carbon / Triethylene glycol dimethyl ether / 4 h / 240 °C / Inert atmosphere
9.1: methanesulfonic acid / 0.5 h / 90 °C / Inert atmosphere
10.1: n-butyllithium; N-cyclohexylisopropylamine / tetrahydrofuran; hexane / -78 °C / Inert atmosphere
10.2: 1 h / -78 °C / Inert atmosphere
11.1: palladium 10% on activated carbon / Triethylene glycol dimethyl ether / 4 h / 240 °C / Inert atmosphere
12.1: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 °C / Inert atmosphere
12.2: Inert atmosphere
13.1: methanesulfonic acid / dichloromethane / 0.5 h / 20 °C / Cooling with ice
With
aluminum (III) chloride; n-butyllithium; methanesulfonic acid; sulfuric acid; N-cyclohexylisopropylamine; palladium 10% on activated carbon; diisobutylaluminium hydride; hydrazine hydrate;
In
tetrahydrofuran; Triethylene glycol dimethyl ether; hexane; dichloromethane; toluene; 1,1,2,2-tetrachloroethane; diethylene glycol;
2.1: Wolff-Kishner reduction / 2.2: Wolff-Kishner reduction / 4.1: Wolff-Kishner reduction / 4.2: Wolff-Kishner reduction / 5.1: Friedel-Crafts acylation / 6.1: Wolff-Kishner reduction / 6.2: Wolff-Kishner reduction;
DOI:10.1039/c0ob01107j