Multi-step reaction with 13 steps
1: 64 percent / DIBALH / CH2Cl2; benzene / 1.) 0 deg C, 10 min, 2.) 22 deg C, 20 h
2: 70 percent / DDQ / CH2Cl2; H2O / 0.5 h / 22 °C
3: 87 percent / 2,6-lutidine, DMAP / 8 h / 70 °C
4: 40 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -25 deg C, 1.5 h, 2.) -78 deg C, 5 min
5: 99 percent / 2percent HCl / methanol; CH2Cl2 / 0.08 h / 22 °C
6: 83 percent / CaCO3, aq. Hg(ClO4)2 / tetrahydrofuran / 2.5 h / 22 °C
7: 45 percent / 2percent HCl / 21 h / 78 °C
8: 30 percent / 49percent aq. HF / nitromethane / 24 h / 0 °C
9: LiOH*H2O / tetrahydrofuran; H2O / 1 h / 22 °C
10: tetrahydrofuran / 1.5 h / 55 °C
11: 21 percent / CSA / CH2Cl2 / 0.75 h / 22 °C
12: DMAP, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 10.5 h / 22 °C
13: 79 percent / pyridine / CH2Cl2 / 0.17 h / 22 °C
With
pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; lithium hydroxide; n-butyllithium; mercury(II) perchlorate; camphor-10-sulfonic acid; hydrogen fluoride; diisobutylaluminium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; calcium carbonate;
In
tetrahydrofuran; methanol; nitromethane; hexane; dichloromethane; water; benzene;