Multi-step reaction with 11 steps
1.1: n-butyllithium; potassium tert-butylate / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere
1.2: 0.75 h / -78 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / dichloromethane; ethanol / 50 °C
3.1: triethylamine / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 2 h / 65 °C / Inert atmosphere
5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 60 °C / Inert atmosphere
6.1: N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C
7.1: sodium tetrahydroborate / diethylene glycol dimethyl ether / 1 h / 0 °C
8.1: perchloric acid / water / 1 h / 0 °C
9.1: hydrogen; palladium on activated charcoal / ethyl acetate / 48 h
10.1: triethylamine / dichloromethane / 1 h / -78 °C / Inert atmosphere
11.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 85 °C / Inert atmosphere
With
sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; perchloric acid; palladium on activated charcoal; potassium tert-butylate; hydrogen; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine;
In
tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; diethylene glycol dimethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;