Multi-step reaction with 7 steps
1.1: 1-chloroethyl chloroformate / 1,2-dichloro-ethane / 1 h / Heating
1.2: MeOH / 0.75 h / Heating
2.1: 6.14 g / aq. NaHCO3 / acetone
3.1: NaH / dimethylformamide / 1 h / 20 °C
3.2: 85 percent / dimethylformamide / 24 h / 25 °C
4.1: 73 percent / ICl; NaN3 / acetonitrile; dimethylformamide / 70 h / Heating
5.1: 64 percent / toluene / 1 h
6.1: 94 percent / 2,6-lutidine; TMSOTf / CH2Cl2 / 0.75 h / 20 °C
7.1: 83 percent / pyridine / 0.5 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; sodium azide; carbonochloridic acid 1-chloro-ethyl ester; trimethylsilyl trifluoromethanesulfonate; Iodine monochloride; sodium hydride; sodium hydrogencarbonate;
In
dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1039/b405768f