Multi-step reaction with 10 steps
1: sodium iodide / butanone / 17 h / 85 °C
2: 18-crown-6 ether / acetic acid / 120 h / 100 °C
3: chlorosulfonic acid / dichloromethane / -80 - 5 °C
4: oxalyl dichloride / N,N-dimethyl-formamide / 3 h / -10 - 5 °C
5: sulfuric acid; potassium nitrate / 0.25 h / -12 °C
6: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.33 h / 0 °C
7: water; caesium carbonate / methanol / 2.5 h / 0 - 20 °C
8: toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 1.5 h
9: pyridine / dichloromethane / 2.5 h / 0 °C / Inert atmosphere
10: methanol / dichloromethane / 15 h
With
pyridine; methanol; chlorosulfonic acid; oxalyl dichloride; 18-crown-6 ether; sulfuric acid; water; caesium carbonate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium nitrate; N-ethyl-N,N-diisopropylamine; sodium iodide;
In
methanol; dichloromethane; N,N-dimethyl acetamide; acetic acid; N,N-dimethyl-formamide; butanone;
DOI:10.1021/jm201717y