Multi-step reaction with 11 steps
1.1: iodine; silver nitrate / methanol / 1 h / 760.05 Torr
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / 760.05 Torr
2.2: 0.17 h / 20 °C / 760.05 Torr
3.1: piperidine; acetic acid / benzene / 760.05 Torr / Reflux
4.1: 4-methyl-morpholine / isopropyl alcohol / 90 °C / 760.05 Torr
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C / 760.05 Torr
6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0.08 h / 0 °C / 760.05 Torr
7.1: pyridinium chlorochromate / dichloromethane / 20 °C / 760.05 Torr
8.1: caesium carbonate / methanol; hexane / 60 °C / 760.05 Torr
9.1: caesium carbonate / N,N-dimethyl-formamide / 1.25 h / 80 °C / 760.05 Torr
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C / 760.05 Torr / Cooling with ice
11.1: pyridinium chlorochromate / dichloromethane / 1.5 h / 20 °C / 760.05 Torr
With
piperidine; 4-methyl-morpholine; lithium aluminium tetrahydride; n-butyllithium; iodine; caesium carbonate; silver nitrate; acetic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; benzene;