Multi-step reaction with 9 steps
1.1: magnesium; copper(I) bromide / tetrahydrofuran / 4 h / 0 - 20 °C
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere
3.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 h / 20 °C
4.1: benzyltriethylammonium chloride / 0.05 h
4.2: 22.58 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere
5.2: 0.5 h / Inert atmosphere
5.3: 3 h / Inert atmosphere
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / -10 °C
8.1: sodium L-ascorbate; copper(ll) sulfate pentahydrate / N,N-dimethyl-formamide; water / 85 °C
9.1: hydrogenchloride / water; tetrahydrofuran; methanol / 3 h / 20 °C
With
hydrogenchloride; n-butyllithium; copper(ll) sulfate pentahydrate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; magnesium; benzyltriethylammonium chloride; sodium L-ascorbate; N-ethyl-N,N-diisopropylamine; copper(I) bromide;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.ejmech.2014.03.062