Multi-step reaction with 7 steps
1: 1.) sodium hydride / 1.) DMF, 0 deg C, 30 min, 2.) DMF, room temperature, 1 h
2: 1.) sodium hydride / 1.) DMF, 0 deg C, 30 min, 2.) DMF, room temperature, 1 h
3: 96 percent / pyridinium p-toluenesulfonate / ethanol / 1 h / Heating
4: 1.) triphenylphosphine, imidazole, 2.) iodine / 1.) toluene, acetonitrile, room temperature -> 50 deg C, 2.) toluene, acetonitrile, 70 deg C, 1 h
5: 93 percent / zinc / methanol / 1.5 h / Heating
6: 1.) sodium hexamethyldisilazide / 1.) THF, room temperature -> -78 deg C, 2.) THF, -78 deg C, 1.5 h
7: 1.) n-butyllithium / 1.) ether, 2 min, 2.) ether, -78 deg C -> room temperature
With
1H-imidazole; n-butyllithium; iodine; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; triphenylphosphine; zinc;
In
methanol; ethanol;
DOI:10.1021/jo981749j