Multi-step reaction with 11 steps
1: lithium hydride / dimethyl sulfoxide / 48 h / 20 °C
2: dipotassium peroxodisulfate; copper(ll) sulfate pentahydrate / water; acetonitrile / 0.67 h / Heating / reflux
3: sodium ethanolate / ethanol / 48 h / 20 °C
4: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chlorobenzene / 1 h / 20 - 85 °C
5: acetonitrile / 1 h / Heating / reflux; Inert atmosphere
6: ethyloxirane; acetonitrile / 15 h / Heating / reflux
7: hydrogen / palladium 10% on activated carbon / ethyl acetate / 36 h / 20 °C / 760.05 Torr
8: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C
9: carbon tetrabromide; triphenylphosphine / dichloromethane / 3 h / 0 - 10 °C
10: pyridine N-oxide; sodium hydrogencarbonate / toluene / 24 h / Heating / reflux
11: potassium carbonate / methanol / 0 - 20 °C
With
pyridine N-oxide; dipotassium peroxodisulfate; N-Bromosuccinimide; copper(ll) sulfate pentahydrate; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; sodium ethanolate; lithium hydride; sodium hydrogencarbonate; potassium carbonate; triphenylphosphine;
palladium 10% on activated carbon;
In
tetrahydrofuran; ethyloxirane; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; chlorobenzene; toluene; acetonitrile;
3: Horner-Wadsworth-Emmons Olefination / 5: Wittig Reaction / 6: Wittig Reaction / 11: Ohira alkynylation;