Multi-step reaction with 9 steps
1.1: 94 percent / lithium aluminum hydride / tetrahydrofuran / 0 - 20 °C
2.1: 96 percent / imidazole / dimethylformamide / 2 h / 20 °C
3.1: 97 percent / sodium hydride / dimethylformamide
4.1: 99 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
5.1: 87 percent / pyridinium chlorochromate / CH2Cl2 / 20 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
6.2: 82 percent / tetrahydrofuran; hexane / 2 h / -78 °C
7.1: 92 percent / Grubbs' second generation catalyst / CH2Cl2 / 2 h / Heating
8.1: 94 percent / hydrogen / Pd/C / ethanol / 10 h / 20 °C
9.1: 80 percent / sodium amalgam; sodium phosphate / methanol / 5 h / 20 °C
With
1H-imidazole; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium phosphate; pyridinium chlorochromate;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2006.09.004