Multi-step reaction with 7 steps
1.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -10 °C / Inert atmosphere
1.2: 0.5 h / 20 °C / Inert atmosphere
2.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 3.5 h / 20 °C / Inert atmosphere
3.1: hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium hexacyanoferrate(III); potassium carbonate; potassium dioxido(dioxo)osmium hydrate; methanesulfonamide / water; tert-butyl alcohol / 19 h / 0 °C
4.1: triethylamine; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
5.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere
6.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
6.2: 0.17 h / -78 °C / Inert atmosphere
6.3: 1 h / -78 °C / Inert atmosphere
7.1: quinoline; hydrogen / ethyl acetate / 1 h / 50 °C
With
quinoline; dmap; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; methanesulfonamide; potassium dioxido(dioxo)osmium hydrate; potassium hexacyanoferrate(III); hydrogen; sodium hydrogencarbonate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/jo3016055