Multi-step reaction with 10 steps
1.1: aluminum (III) chloride / chloroform / 0.5 h / 0 °C / Inert atmosphere
1.2: 4 h / 0 - 20 °C / Inert atmosphere
2.1: sodium hydroxide; water / toluene / 1.5 h / 50 - 60 °C / Inert atmosphere
3.1: hydrazine hydrate; potassium hydroxide / 16 h / -50 - 100 °C / Inert atmosphere
4.1: potassium carbonate; pivaloyl chloride / acetone / 0.33 h / -10 - 20 °C / Inert atmosphere
5.1: lithium hexamethyldisilazane; n-butyllithium / hexane; tetrahydrofuran / 1 h / -45 - 0 °C / Inert atmosphere
5.2: 3 h / -45 - 0 °C / Inert atmosphere
6.1: pyridinium p-toluenesulfonate / ethanol / 2 h / 50 °C / Inert atmosphere
7.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 0.33 h / 25 °C / Molecular sieve; Inert atmosphere
8.1: hydrogenchloride / water; 1,4-dioxane / 18 h / 120 °C / Inert atmosphere
9.1: formic acid; dihydrogen peroxide / water / 1 h / 0 °C / Inert atmosphere
10.1: potassium permanganate / water; methanol / 1 h / 25 °C / Inert atmosphere
With
hydrogenchloride; aluminum (III) chloride; potassium permanganate; n-butyllithium; formic acid; tetrapropylammonium perruthennate; water; dihydrogen peroxide; pyridinium p-toluenesulfonate; pivaloyl chloride; potassium carbonate; hydrazine hydrate; 4-methylmorpholine N-oxide; potassium hydroxide; sodium hydroxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; chloroform; water; acetone; toluene;
DOI:10.1021/jm3008689