Multi-step reaction with 9 steps
1.1: ammonium hydroxide; zinc(II) chloride / water / 108 h / 190 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / n-heptan1ol / 19 h / Inert atmosphere; Reflux
3.1: zinc(II) chloride; N-Bromosuccinimide / acetone / 2 h / -78 °C / Inert atmosphere
4.1: potassium carbonate; copper(l) chloride / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere
5.1: palladium on activated charcoal; hydrogen; quinoline / acetone / 2.5 h / 20 °C / 760.05 Torr / Inert atmosphere
6.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide; 1,4-diaza-bicyclo[2.2.2]octane / water; acetone / 72 h / 0 °C / Inert atmosphere
7.1: pyridine / 0.5 h / 0 °C / Inert atmosphere
7.2: 1 h
7.3: 3 h / 20 °C
8.1: n-butyllithium / tetrahydrofuran; hexane / 20 h / -78 - 20 °C / Inert atmosphere
9.1: triphenylphosphine; tetrachloromethane / 1,2-dichloro-ethane / 18 h / 50 °C / Inert atmosphere
With
pyridine; 1,4-diaza-bicyclo[2.2.2]octane; quinoline; tetrachloromethane; potassium osmate(VI) dihydrate; ammonium hydroxide; N-Bromosuccinimide; n-butyllithium; palladium on activated charcoal; hydrogen; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triphenylphosphine; copper(l) chloride; zinc(II) chloride;
In
tetrahydrofuran; hexane; n-heptan1ol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;
DOI:10.3987/COM-12-S(N)37