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: potassium carbonate / N,N-dimethyl-formamide; acetone / 24 h / 70 °C
10.1: caesium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane / 5 h / 78 °C
11.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C
12.1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane; N,N-dimethyl-formamide / 4 h / 20 °C
13.1: water; sodium hydroxide / ethanol / 3 h / 20 °C
13.2: Acidic aqueous solution
With
dipotassium peroxodisulfate; N-Bromosuccinimide; copper(ll) sulfate pentahydrate; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tetrabutyl ammonium fluoride; water; hydrogen; sodium ethanolate; potassium carbonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; sodium hydroxide;
tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon;
In
tetrahydrofuran; ethyloxirane; 1,2-dimethoxyethane; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; chlorobenzene; acetone; acetonitrile;
2.1: Horner-Wadsworth-Emmons Olefination / 4.1: Wittig Reaction / 5.1: Wittig Reaction / 10.1: Suzuki Coupling;