Multi-step reaction with 9 steps
1.1: caesium carbonate / N,N-dimethyl-formamide / 90 °C / Sealed tube
2.1: hydrogen; palladium 10% on activated carbon / methanol / 8 h
3.1: sodium hydroxide / methanol; water / 20 °C
4.1: triethylamine / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere
5.1: n-butyllithium / hexane; tetrahydrofuran / -78 °C / Inert atmosphere
5.2: -78 - 20 °C / Inert atmosphere
6.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere
6.2: -78 °C / Inert atmosphere
6.3: -78 - 30 °C / Inert atmosphere
7.1: dihydrogen peroxide; lithium hydroxide / water; tetrahydrofuran / 2.5 h / 0 °C
8.1: hydrogen; palladium 10% on activated carbon / methanol; water / 6 h
9.1: sodium hydrogencarbonate / water; 1,4-dioxane / 0 - 20 °C
With
n-butyllithium; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; sodium hydrogencarbonate; caesium carbonate; triethylamine; sodium hydroxide; lithium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1055/s-0033-1339892