Multi-step reaction with 9 steps
1.1: potassium tert-butylate / tetrahydrofuran / 20 °C / Reflux
1.2: 2 h / Reflux
1.3: pH 12
2.1: dmap / dichloromethane / 20 °C
3.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 3 h / Reflux
4.1: potassium carbonate / N,N-dimethyl-formamide; tetrahydrofuran
5.1: hydrazine hydrate / ethanol / 3.5 h
6.1: lithium hexamethyldisilazane / N,N-dimethyl-formamide; tetrahydrofuran / 0.08 h / Inert atmosphere
6.2: 80 °C / Inert atmosphere; sealed tube
7.1: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C
8.1: lithium hexamethyldisilazane / N,N-dimethyl-formamide; tetrahydrofuran / 11.5 h / 100 °C / Inert atmosphere; sealed tube
9.1: lithium hydroxide monohydrate / acetonitrile; water; tetrahydrofuran / 20 °C
With
N-Bromosuccinimide; lithium hydroxide monohydrate; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; potassium carbonate; hydrazine hydrate; trifluoroacetic acid; lithium hexamethyldisilazane;
dmap;
In
tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;