Multi-step reaction with 9 steps
1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
1.2: 6 h / 20 °C / Inert atmosphere
2.1: acetic acid / water / 12 h / 20 °C
3.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
3.2: 4 h / 20 °C / Inert atmosphere
4.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere
5.1: copper(l) iodide / tetrahydrofuran / 0.17 h / Inert atmosphere
5.2: 1 h / -20 °C / Inert atmosphere
6.1: 1H-imidazole / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
6.2: 12 h / 20 °C / Inert atmosphere
7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 0.33 h / 0 - 20 °C / Inert atmosphere
8.1: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
9.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / tert-butyl alcohol / 2 h / 0 - 20 °C
With
1H-imidazole; sodium chlorite; copper(l) iodide; sodium dihydrogenphosphate dihydrate; oxalyl dichloride; water; sodium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol;
8.1: |Swern Oxidation;
DOI:10.1002/hlca.201200064