Multi-step reaction with 9 steps
1: 90 percent / NH4NO3 / methanol / 2 h / Heating
2: 88 percent / SiO2; aq. H2SO4 / CH2Cl2 / 0.75 h / 20 °C
3: 85 percent / NaOH / CH2Cl2 / 4 h / 20 °C
4: 97 percent / HMPA / tetrahydrofuran / 7 h / 0 - 20 °C
5: 97 percent / imidazole / dimethylformamide / 24 h / 20 °C
6: 100 percent / SiO2; aq. H2SO4 / CH2Cl2 / 1.5 h / 20 °C
7: 97 percent / H2 / Lindlar's catalyst / pyridine; hexane / 1.33 h / 20 °C
8: LiHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / 1.5 h / -80 °C
9: Na2CO3 / hexamethylphosphoric acid triamide; tetrahydrofuran / 12 h / 20 °C
With
1H-imidazole; ammonium nitrate; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sulfuric acid; hydrogen; silica gel; sodium carbonate; lithium hexamethyldisilazane;
Lindlar's catalyst;
In
tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; N,N-dimethyl-formamide;
8: Wittig reaction;
DOI:10.1016/S0040-4039(02)01056-0