Multi-step reaction with 13 steps
1.1: dipotassium peroxodisulfate; copper(ll) sulfate pentahydrate / water; acetonitrile / 0.67 h / Heating / reflux
2.1: sodium ethanolate / ethanol / 48 h / 20 °C
3.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chlorobenzene / 1 h / 20 - 85 °C
4.1: acetonitrile / 1 h / Heating / reflux; Inert atmosphere
5.1: ethyloxirane; acetonitrile / 15 h / Heating / reflux
6.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 36 h / 20 °C / 760.05 Torr
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C
8.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 3 h / 0 - 10 °C
9.1: pyridine N-oxide; sodium hydrogencarbonate / toluene / 24 h / Heating / reflux
10.1: potassium carbonate / methanol / 0 - 20 °C
11.1: water; sodium hydroxide / ethanol / 5 h / 20 °C
11.2: Acidic aqueous solution
12.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 5 h / 70 °C
12.2: 20 °C
13.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water / 5 h / 78 °C
With
pyridine N-oxide; dipotassium peroxodisulfate; N-Bromosuccinimide; copper(ll) sulfate pentahydrate; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tetrabutyl ammonium fluoride; water; hydrogen; sodium ethanolate; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; sodium hydroxide;
bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon;
In
tetrahydrofuran; ethyloxirane; methanol; ethanol; dichloromethane; water; ethyl acetate; chlorobenzene; toluene; acetonitrile;
2.1: Horner-Wadsworth-Emmons Olefination / 4.1: Wittig Reaction / 5.1: Wittig Reaction / 10.1: Ohira alkynylation / 12.1: Sonogashira Coupling / 13.1: Suzuki Coupling;