Multi-step reaction with 16 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h
2.1: n-butyllithium / tetrahydrofuran; hexane / 1.75 h / -70 °C / Inert atmosphere
2.2: 0.5 h / 20 °C
3.1: hydrogenchloride; water / tetrahydrofuran; hexane / 16 h / 60 °C
4.1: N-Bromosuccinimide / acetonitrile / 1 h / 0 °C
5.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C
6.1: Amberlyst-15 / hexane / 3 h / Reflux
7.1: magnesium / tetrahydrofuran / 1.5 h / 20 °C
7.2: 1 h / 0 °C
7.3: 16 h / 20 °C
8.1: thionyl chloride / N,N-dimethyl-formamide / toluene / 6.5 h / 60 °C
9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 14 h / 20 °C
10.1: Amberlyst-15 / ethanol / 3.5 h / Reflux
11.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C
12.1: hydrogenchloride / ethyl acetate / 2 h / 20 °C
13.1: sodium chlorite; 2-methyl-but-2-ene; citric acid / methanol; water / 1 h / 20 °C
14.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 19 h / 20 °C
15.1: lithium chloride / N,N-dimethyl-formamide / 1.5 h / 120 °C
16.1: Oxone / tetrahydrofuran; water / 1 h / 20 °C
With
hydrogenchloride; Oxone; sodium chlorite; N-Bromosuccinimide; n-butyllithium; thionyl chloride; 2-methyl-but-2-ene; water; potassium carbonate; magnesium; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; citric acid; lithium chloride;
N,N-dimethyl-formamide;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;