Multi-step reaction with 9 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C
1.2: 3 h / -78 - -40 °C
1.3: pH < 1
2.1: acetic acid / 100 °C / Sealed tube
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 45 °C
4.1: 2,6-dimethylpyridine; sodium periodate / osmium(VIII) oxide / 1,4-dioxane; water / 20 °C
5.1: -20 - 20 °C
6.1: N-iodo-succinimide / acetonitrile / 1 h / 20 °C
7.1: potassium phosphate monohydrate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 16 h / 90 °C / Inert atmosphere
8.1: N-Bromosuccinimide / acetonitrile / 0.5 h / 20 °C
9.1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
With
2,6-dimethylpyridine; sodium periodate; N-Bromosuccinimide; N-iodo-succinimide; n-butyllithium; potassium phosphate monohydrate; N-ethyl-N,N-diisopropylamine;
osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetic acid; acetonitrile;