Multi-step reaction with 11 steps
1: 93 percent / 2,6-lutidine / CH2Cl2 / Ambient temperature
2: 6.05 g / Hg(ClO4)2, CaCO3 / tetrahydrofuran; H2O / 0.75 h / Ambient temperature
3: 7.72 g / benzene / 50 °C
4: 99 percent / H2 / Pd/C / ethanol / 5 h / Ambient temperature
5: 83 percent / LDA / tetrahydrofuran / 1 h / -30 °C
6: 88 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C
7: 100 percent / pyridine / Ambient temperature
8: 89 percent / NaI / acetone / Heating
9: 100 percent / t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 1 h / -78 °C
10: 88 percent / n-Bu4NF / tetrahydrofuran / Ambient temperature
11: 100 percent / imidazole, 4-dimethylaminopyridine / dimethylformamide / 50 °C
With
1H-imidazole; 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; mercury(II) perchlorate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; calcium carbonate; sodium iodide; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; pentane; benzene;
DOI:10.1246/bcsj.71.2433