Multi-step reaction with 11 steps
1.1: dichloromethane / 0 - 20 °C
2.1: thionyl chloride / dichloromethane / 20 °C / Cooling with ice bath
3.1: diethyl ether; tetrahydrofuran / 0 - 20 °C
4.1: potassium hexamethylsilazane / toluene; tetrahydrofuran / -20 - 15 °C / Inert atmosphere
5.1: acetonitrile / 63 °C
6.1: sodium hydroxide; water / methanol / 1 h / 80 °C
6.2: pH 1
7.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2.75 h
7.2: 4 h
8.1: tetrahydrofuran / 3 h / 63 °C
9.1: potassium tert-butylate / tetrahydrofuran / 2.25 h / 55 - 62 °C
10.1: sodium hydrogencarbonate; copper(l) iodide / ethyl acetate; dimethyl sulfoxide / 3.5 h / 110 °C / Inert atmosphere
11.1: potassium carbonate / tricyclohexylphosphine; bis(dibenzylideneacetone)-palladium(0) / butan-1-ol; 1,4-dioxane; water / 1 h / 100 °C / Inert atmosphere
With
copper(l) iodide; thionyl chloride; potassium tert-butylate; water; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; 1,1'-carbonyldiimidazole; sodium hydroxide;
bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile; butan-1-ol;