Multi-step reaction with 10 steps
1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / Inert atmosphere; Reflux
2.1: copper(l) iodide / diethyl ether / 0.33 h / 0 °C / Inert atmosphere
2.2: 5 h / 0 °C / Inert atmosphere
2.3: Inert atmosphere
3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
3.2: 0.5 h / -78 °C / Inert atmosphere
4.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 3 h / 0 °C / Inert atmosphere
5.1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
6.2: 20 °C / Inert atmosphere
7.1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
8.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere
9.1: sodium iodide / acetone / 48 h / 20 °C / Inert atmosphere
10.1: potassium tert-butylate / tetrahydrofuran / 5 h / 0 °C / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; copper(l) iodide; cerium(III) chloride heptahydrate; potassium tert-butylate; tetrabutyl ammonium fluoride; triethylamine; sodium iodide; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone;
DOI:10.1016/j.tet.2011.06.025