Multi-step reaction with 9 steps
1.1: calcium carbonate / water; 1,4-dioxane / 12 h / 110 °C / Inert atmosphere
2.1: dmap; 1H-imidazole / dichloromethane / 16 h / 23 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C / Inert atmosphere
3.2: 1.5 h / -78 - 23 °C / Inert atmosphere
4.1: toluene-4-sulfonic acid / tetrahydrofuran; water / 14 h / 23 °C / Inert atmosphere
5.1: diphenylphosphoranyl azide; triethylamine / benzene / 1 h / 85 °C / Inert atmosphere
5.2: 3 h / 85 °C / Inert atmosphere
6.1: sodium dihydrogen phosphate monohydrate; sodium chlorite; 2-methyl-but-2-ene / water; acetone / 0.5 h / 23 °C / Inert atmosphere
7.1: diphenylphosphoranyl azide; triethylamine / benzene / 1 h / 85 °C / Inert atmosphere
7.2: 3 h / 85 °C / Inert atmosphere
8.1: toluene-4-sulfonic acid / tetrahydrofuran; water / 14 h / 23 °C / Inert atmosphere
8.2: 24 h / 23 °C / Inert atmosphere
9.1: triethylamine / tetrahydrofuran / 1.5 h / 23 °C / Inert atmosphere
With
1H-imidazole; dmap; sodium chlorite; n-butyllithium; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; diphenylphosphoranyl azide; toluene-4-sulfonic acid; triethylamine; calcium carbonate;
In
tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; acetone; benzene;
5.1: |Curtius Rearrangement / 5.2: |Curtius Rearrangement / 7.1: |Curtius Rearrangement / 7.2: |Curtius Rearrangement;
DOI:10.1021/jo400105m