Multi-step reaction with 9 steps
1: 50 percent / NaH / dioxane / 6 h / Heating
2: aq.LiCl / dimethylsulfoxide / 4 h / Heating
3: 2M NaOEt / 24 h / Ambient temperature
4: BH3 / tetrahydrofuran / 16 h / 0 - 20 °C
5: 95 percent / Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 16 h / Ambient temperature
6: 1.) n-BuLi / 1.) hexane, THF, from -78 deg C to -10 deg C, 2.) THF, hexane, 45 min
7: 1-hydroxybenzotriazole, diisopropylethylamine, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 18 h / Ambient temperature
8: 65 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature
9: 89 percent / CBr4, Ph3P / CH2Cl2 / 16 h / 6 - 20 °C
With
dmap; n-butyllithium; carbon tetrabromide; borane; tetrabutyl ammonium fluoride; sodium ethanolate; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1002/jhet.5570320514