Multi-step reaction with 8 steps
1: 1.) Mg / 1.) THF, 2.) THF, r.t., 2 h
2: 96 percent / hydroxylamine hydrochloride, pyridine / ethanol / 12 h / 60 °C
3: Et3N, (N,N-dimethylamino)pyridine / CH2Cl2 / 0.75 h / Ambient temperature
4: liq. NH3 / CH2Cl2 / 18 h / Ambient temperature
5: 77 percent / tert-butyl hypochlorite, Et3N / ethanol; 2-methyl-propan-2-ol / 2 h / Ambient temperature
6: 92 percent / BBr3 / CH2Cl2 / 7 h / 0 °C
7: K2CO3, 18-crown-6 / tetrahydrofuran / 18 h / Ambient temperature
8: 1.) thallium(III) trifluoroacetate, 2.) NaNO2 / 1.) TFA, r.t., 2.) r.t., 30 min
With
pyridine; dmap; 18-crown-6 ether; tert-butylhypochlorite; hydroxylamine hydrochloride; ammonia; boron tribromide; potassium carbonate; magnesium; triethylamine; sodium nitrite; thallium(III) trifluoroacetate;
In
tetrahydrofuran; ethanol; dichloromethane; tert-butyl alcohol;
DOI:10.1021/jo00081a017