Multi-step reaction with 12 steps
1.1: 2 h / 130 °C
2.1: sodium tetrahydroborate / methanol / 2 h / Cooling with ice; Reflux
3.1: triethylamine / dichloromethane / 20 °C / Cooling with ice
4.1: N-Bromosuccinimide; acetic acid / 20 °C
5.1: potassium carbonate / methanol / 1 h / 20 °C
6.1: triethylamine / dichloromethane / 1 h
7.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Cooling with ice
7.2: 4 h / 65 °C
8.1: sodium tetrahydroborate / methanol / 3 h / 65 °C
8.2: Cooling with ice
9.1: triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice
10.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 16 h / Reflux
11.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere
12.1: potassium carbonate / methanol / 1 h / 20 °C
With
sodium tetrahydroborate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sodium hydride; potassium carbonate; acetic acid; triethylamine;
In
tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; mineral oil;