Multi-step reaction with 11 steps
1: potassium carbonate / acetone / 6 h / Heating
2: acetic acid; ethylenediamine / 20 °C
3: acetic acid; ethylenediamine / 20 °C
4: lithium aluminium tetrahydride / tetrahydrofuran / 24 h / 20 °C
5: sodium carbonate / dichloromethane; water / 2 h / 20 °C
6: trichlorophosphate / N,N-dimethyl-formamide / 3 h / 20 °C
7: sodium hydrogencarbonate / acetonitrile / 18 h / Heating
8: hydrogen / palladium on activated charcoal / ethyl acetate / 20 °C / 3878.61 Torr
9: sodium hydride / tetrahydrofuran / 0 - 20 °C
10: dmap; triethylamine / dichloromethane / 4 h / 20 °C
11: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,2-dichloro-ethane / 18 h / Heating
With
dmap; lithium aluminium tetrahydride; hydrogen; sodium hydride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; acetic acid; ethylenediamine; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; trichlorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; acetonitrile;
2: Knoevenagel reaction / 3: Knoevenagel reaction / 6: Bischler-Napieralski reaction;
DOI:10.1021/jo061810h