Multi-step reaction with 7 steps
1: 40 percent / Tris-HCl buffer, pH 7, PLE, 0.1 M NaOH / dimethylsulfoxide; H2O / 26 h / Ambient temperature
2: 89 percent / Na2CO3 / methanol / 1.5 h / Ambient temperature
3: 1.2 g / imidazole / dimethylformamide / 15 h / Ambient temperature
4: 1.) CuBr*Me2S, HMPA, TMSCl, 2.) NH4Cl, NH4OH, pH 8-9 / 1.) THF, -78 deg C, 3 h; -78 deg C to -50 deg C, 2.5 h, 2.) H2O, Et2O
5: 82 percent / 80percent CF3COOH / dioxane; H2O / 16.5 h / 80 °C
6: 1.) TMSBr, BF3*Et2O, 2.) NH4Cl, NH4OH, pH 8-9 / 1.) THF, -78 deg C, 6.5 h, 2.) H2O, room temperature
7: 80 percent / diethyl ether / 1 h / -20 - -5 °C
With
1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; ammonium hydroxide; sodium hydroxide; chloro-trimethyl-silane; Tris-HCl buffer; copper(I) bromide dimethylsulfide complex; trimethylsilyl bromide; boron trifluoride diethyl etherate; sodium carbonate; ammonium chloride; trifluoroacetic acid;
In
1,4-dioxane; methanol; diethyl ether; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo961605+