Multi-step reaction with 9 steps
1.1: hydrogen; quinoline / Lindlar's catalyst / ethyl acetate / 0.67 h / 760.05 Torr
2.1: diethylzinc / dichloromethane; 1,2-dimethoxyethane / 1.58 h / -30 - -20 °C / Inert atmosphere
2.2: 1 h / -15 - 20 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 0 °C
3.2: 0.5 h / 0 - 20 °C
4.1: n-butyllithium / hexane; diethyl ether / 0.25 h / -78 °C
4.2: 0.5 h / -78 °C
5.1: Oxone / water; methanol / 1 h / 20 °C
6.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C
7.1: caesium carbonate / dimethyl sulfoxide / 20 °C / Inert atmosphere
8.1: sodium tetrahydroborate / methanol / 0.5 h / 20 °C
9.1: sodium hydride / acetonitrile; mineral oil / 20 °C / Inert atmosphere
With
quinoline; hydrogenchloride; Oxone; sodium tetrahydroborate; n-butyllithium; hydrogen; diethylzinc; sodium hydride; caesium carbonate;
Lindlar's catalyst;
In
1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; mineral oil;