Multi-step reaction with 11 steps
1.1: copper(ll) bromide / ethyl acetate; chloroform / 6 h / Reflux
2.1: 15 h / 100 °C / Sealed tube
3.1: lithium borohydride / tetrahydrofuran / 20 °C
4.1: Dess-Martin periodane / dichloromethane / 20 °C
5.1: titanium(IV) tetraethanolate / tetrahydrofuran / 4 h / 20 °C
6.1: pentane; tetrahydrofuran / 3 h / -78 °C
6.2: -78 °C
6.3: -78 °C
7.1: hydrogenchloride; methanol / 1,4-dioxane / 1 h / 20 °C
8.1: sodium tris(acetoxy)borohydride / dichloromethane / 0.33 h / 20 °C
9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C
10.1: potassium carbonate; methanol / 0.5 h / 20 °C
11.1: hydrogen / palladium on activated charcoal / ethanol / 30 h / 20 °C / Inert atmosphere
With
hydrogenchloride; methanol; titanium(IV) tetraethanolate; lithium borohydride; hydrogen; sodium tris(acetoxy)borohydride; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; copper(ll) bromide;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; chloroform; ethyl acetate; pentane;