Multi-step reaction with 7 steps
1: 99.9 percent / i-Pr2NEt / CH2Cl2 / 18 h / Heating
2: 100 percent / 3 N aq. NaOH / methanol / 2 h / Ambient temperature
3: 95.4 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 60 h / Ambient temperature
4: 1.) n-BuLi, 2.) I2 / 1.) hexane, 0 deg C, 3.5 h, 2.) hexane, Et2O, 0 deg C, 30 min
5: pyridinium p-toluenesulfonate / ethanol / 1.5 h / 70 °C
6: 1.) NaH, 2.) n-Bu4NI / 1.) THF, RT, 30 min, 2.) THF, RT, 1.5 h
7: 97.1 percent / 4 N aq. HCl / methanol; dioxane / 5 h / 50 °C
With
hydrogenchloride; sodium hydroxide; n-butyllithium; iodine; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; N-ethyl-N,N-diisopropylamine;
In
1,4-dioxane; methanol; ethanol; dichloromethane;
DOI:10.1021/ja00082a023