Multi-step reaction with 12 steps
1: 84 percent / KI, K2CO3 / dimethylformamide / 4 h
2: Zn, CaCl2, ethanol / 1.5 h / Heating
3: 80 percent / pyridine / CH2Cl2 / 2 h / 25 °C
4: 80 percent / potessium tert-butoxide / dimethylformamide / 3 h / Ambient temperature
5: 82 percent / 50percent aq. KOH / ethanol / 8 h / Heating
6: 1.) NaNO2, HCl, SnCl2 / 1.) 2 h, 2.) RT, 12 h
7: 1.) NaH / 1.) THF, 0 deg C, 1 h, 2.)THF, RT, 8 h
8: ammonium nitrate, trifluoroacetic anhydride / CHCl3 / 6 h
9: BBr3, cyclohexane / CH2Cl2 / 0.5 h / -20 °C
10: 78 percent / pyridine / CH2Cl2 / 1 h / Ambient temperature
11: 1.) CaCl2, Zn, aq. C2H5OH, 2.) isoamyl nitrite / 1.) 1 h, reflux, 2.) 0 deg C, 15 min, RT, 1h
12: 10 percent / CuSO4, NaNO2 / CH2Cl2 / 0.5 h / Irradiation
With
pyridine; hydrogenchloride; potassium hydroxide; ammonium nitrate; ethanol; cyclohexane; potassium tert-butylate; boron tribromide; sodium hydride; potassium carbonate; copper(II) sulfate; trifluoroacetic anhydride; potassium iodide; calcium chloride; tin(ll) chloride; zinc; sodium nitrite; isopentyl nitrite;
In
ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jo00256a036