Multi-step reaction with 7 steps
1: 66 percent / imidazole / CH2Cl2 / 12 h / Ambient temperature
2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, from -78 deg C to RT
3: aq. Bu4NF / tetrahydrofuran / 0.5 h / Ambient temperature
4: 81.5 percent / Et3N, DMAP / CH2Cl2 / 12 h / Ambient temperature
5: 86 percent / NaN3, tricaprylmethylammonium chloride / benzene / 12 h / 65 °C
6: 1.) TMSBr, 2.) oxalyl chloride, DMF / 1.) CH2Cl2, 45 deg C, 20 min, 2.) CH2Cl2, RT, 20 min
7: 1.) 1H-tetrazole, N,N-diisopropylethylamine, / 1.) benzene, RT, 12 h, 2.) benzene, 20 min
With
1H-imidazole; 1H-tetrazole; dmap; n-butyllithium; sodium azide; oxalyl dichloride; trimethylsilyl bromide; tetrabutyl ammonium fluoride; Aliquat 336; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide;
In
tetrahydrofuran; dichloromethane; benzene;
DOI:10.1021/ja953077+