Multi-step reaction with 10 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C / Inert atmosphere
2.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere
2.2: 0.25 h / -40 - 20 °C / Molecular sieve; Inert atmosphere
3.1: sodium azide / N,N-dimethyl-formamide / 16 h / 60 °C / Inert atmosphere
4.1: pyridine; pyridine hydrogenfluoride / dichloromethane / 2 h / 0 °C / Inert atmosphere
5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 °C / Inert atmosphere
6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; methanol / 3 h / 20 °C / Inert atmosphere
7.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere
7.2: 0.25 h / -40 - 20 °C / Molecular sieve; Inert atmosphere
8.1: pyridine hydrogenfluoride / Inert atmosphere
9.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere
10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; methanol / 4 h / 20 °C / Inert atmosphere
With
pyridine; sodium azide; sodium hydride; pyridine hydrogenfluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1039/c3ob40958a