Multi-step reaction with 10 steps
1: HONH2*HCl, pyridine / ethanol
2: 75 percent / triethylamine / CCl4 / 1) 2 deg C, 15 min, 2) 25 deg C, 1 h
3: benzene / 2 h / 25 °C
4: potassium tert-butoxide / tetrahydrofuran / 1 h / -30 °C
5: 91 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 1 h / 25 °C
6: 95 percent / 4 N aq. LiOH / tetrahydrofuran / 1 h / 25 °C
7: 95 percent / DMF, NaH / 1) 0 deg C to 25 deg C, 10 min, 2) 45 min
8: 76 percent / LiOH / dimethylsulfoxide; H2O / 20 h / Heating
9: diphenyl phosphorazidate, triethylamine / benzene / 1) 25 deg C, 15 min, 2) reflux, 7 h
10: 4 N aq. LiOH / tetrahydrofuran / 1 h / 25 °C
With
pyridine; lithium hydroxide; diphenyl phosphoryl azide; hydroxylamine hydrochloride; potassium tert-butylate; sodium hydride; triethylamine; N,N-dimethyl-formamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; water; dimethyl sulfoxide; benzene;
DOI:10.1021/jo00002a077