Multi-step reaction with 11 steps
1.1: hydrogenchloride; sodium nitrite; tin(ll) chloride / -5 - 20 °C
2.1: acetic acid / ethanol / 1 h / 80 °C
3.1: polyphosphoric acid / toluene / 5 h / 100 °C
4.1: sodium hydride / tetrahydrofuran / 0.67 h / 0 °C
5.1: hydrazine hydrate / ethanol / 0.75 h / 80 °C
6.1: ethanol / 3 h / 80 °C
7.1: potassium hydroxide / water / 2 h / 110 °C
8.1: potassium carbonate / N,N-dimethyl-formamide / 0.01 h / 20 °C
8.2: 20 °C
9.1: trichlorophosphate / -5 °C
9.2: 1 h / 55 °C
10.1: acetic acid / 1,2-dichloro-ethane / 1 h
11.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 4 h / 20 °C
With
hydrogenchloride; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; hydrazine hydrate; acetic acid; tin(ll) chloride; potassium hydroxide; sodium nitrite; trichlorophosphate;
In
tetrahydrofuran; ethanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
9.1: |Vilsmeier-Haack Formylation / 9.2: |Vilsmeier-Haack Formylation;
DOI:10.1016/j.ejmech.2013.08.018