Multi-step reaction with 7 steps
1: 91 percent / pyridine / 16 h / 10 °C
2: 100 percent / dimethylsulfoxide / Ambient temperature
3: 88 percent / aq. KOH / ethanol / 24 h / Heating
4: 1.) 1,1'-carbonyldiimidazole / 1.) CH2Cl2, r.t., 1 h, 2.) H2O, overnight
5: 32 percent / 50percent aq. NaOH, n-Bu4NHSO4 / benzene / 1.) r.t., 45 min, 2.) 3 h
6: 22 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 30 min; to 0 deg C, 30 min, 2.) -78 deg C, 1 h; to r.t., 1 h
7: 79 percent / MsN3, Et3N / acetonitrile / Ambient temperature
With
pyridine; potassium hydroxide; sodium hydroxide; n-butyllithium; tetra(n-butyl)ammonium hydrogensulfate; triethylamine; Methanesulfonyl azide; 1,1'-carbonyldiimidazole;
In
tetrahydrofuran; ethanol; hexane; dimethyl sulfoxide; acetonitrile; benzene;
DOI:10.1021/jo00102a037