Multi-step reaction with 10 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
2.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere
3.1: Jones reagent / acetone / 0 °C
4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 0 - 5 °C
4.2: 0 - 20 °C / Inert atmosphere
5.1: thionyl chloride / toluene / 20 °C / Inert atmosphere; Reflux
6.1: hydrogen / palladium 10% on activated carbon / acetic acid / 6 h / 3102.97 Torr
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 °C
8.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 20 °C
9.1: sodium hydroxide; water / methanol / 20 °C
10.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16.25 h / 20 °C / Inert atmosphere
With
dmap; Jones reagent; thionyl chloride; oxalyl dichloride; di-isopropyl azodicarboxylate; water; hydrogen; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; sodium hydroxide;
palladium 10% on activated carbon; N,N-dimethyl-formamide;
In
tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; toluene;
3.1: Jones Oxidation;