Multi-step reaction with 6 steps
1: 1.) Bu2SnO, 2.) CsF / 1.) toluene, reflux, 2 h, 2.) DMF, -15 deg C, 1 h
2: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) 40 deg C, 2 h
3: 87 percent / AcCl / methanol; CH2Cl2 / 1 h / 23 °C
4: 1.) Bu2SnO, 2.) CsF, NaI / 1.) toluene, reflux, 2 h, 2.) DMF, -15 deg C, 1 h; room temperature, 16 h
5: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) 40 deg C, 2 h
6: 1.) RhCl(PPh3)3, diazabicyclo<2.2.2>octane, 2.) 1N HCl / 1.) EtOH, reflux, 4 h, 2.) acetone, reflux, 30 min
With
1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; RhCl(PPh3)3; sodium hydride; di(n-butyl)tin oxide; acetyl chloride; cesium fluoride; sodium iodide;
In
methanol; dichloromethane;
DOI:10.1021/jo980356h