Multi-step reaction with 11 steps
1.1: thionyl chloride / dichloromethane / 20 °C / Cooling with ice
2.1: tetrahydrofuran; diethyl ether / 8 h / 0 - 20 °C
3.1: potassium hexamethylsilazane / tetrahydrofuran / 2 h / -20 - 15 °C / Inert atmosphere
4.1: acetonitrile / 63 °C
5.1: sodium hydroxide; water / methanol / 1 h / 80 °C
6.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2.75 h
6.2: 4 h
7.1: tetrahydrofuran / 3 h / 63 °C
8.1: potassium tert-butylate / tetrahydrofuran / 2.25 h / 55 - 62 °C
9.1: sodium hydrogencarbonate; copper(l) iodide / dimethyl sulfoxide / 3.5 h / 110 °C / Inert atmosphere
10.1: tricyclohexylphosphine; bis(dibenzylideneacetone)-palladium(0); potassium carbonate / 1,4-dioxane; water; butan-1-ol / 1 h / 110 °C / Inert atmosphere
11.1: sodium tetrahydroborate; methanol / dichloromethane / 0.12 h / 20 °C / Cooling with ice
With
methanol; sodium tetrahydroborate; 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; acetonitrile; butan-1-ol;