Multi-step reaction with 6 steps
1: 65 percent / PBr3, pyridine / benzene / 56 h
2: sodium azide, NaI / dimethylformamide / 18 h / 60 °C
3: 1.) Ph3P, 2.) H2O / 1.) THF, RT, 10 h, 2.) THF, RT, 24 h
4: aq. K2CO3 / tetrahydrofuran / 4 h / Ambient temperature; 1.) THF,water, RT, 2 h, 2.) THF, water, RT, 4 h
5: 11.4 g / K2CO3, tetra-n-butylammonium iodide / tetrahydrofuran / 2 h / Heating
6: 5.91 g / sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 4 h / Heating
With
pyridine; sodium azide; water; phosphorus tribromide; tetra-(n-butyl)ammonium iodide; potassium carbonate; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium iodide;
In
tetrahydrofuran; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jm00007a004