Multi-step reaction with 9 steps
1: NaH / dimethylformamide / 0 - 20 °C
2: CH2Cl2; hexane / 0 - 20 °C
3: 89 percent / NaH, tetrabutylammonium iodide / dimethylformamide / 1.) r.t., 2 h, 2.) r.t., 20 h
4: 92 percent / HCl, H2O / CHCl3; methanol / 10 h / 25 °C
5: 24 percent / pyridine, DMAP / CH2Cl2 / 24 h / 0 °C
6: 90 percent / LiOH, H2O / tetrahydrofuran / 19 h / Ambient temperature
7: 1H-tetrazole / CH2Cl2 / 1.33 h / Ambient temperature
8: mCPBA / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) r.t., 1 h
9: 93 percent / (NH4)2Ce(NO2)6, H2O / acetonitrile / 0.75 h / 0 °C
With
pyridine; 1H-tetrazole; hydrogenchloride; dmap; lithium hydroxide; ammonium cerium(IV) nitrate; water; tetra-(n-butyl)ammonium iodide; sodium hydride; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;