Multi-step reaction with 7 steps
1: 1.) lithium diisopropylamide, 3.) aq. HCl / 1) THF, hexane, -78 deg C --> rt, 1 h; 2) THF, hexane, rt, 3 h; 3) 10 min
2: 1.) NaH / 1) DMF, rt, 4 h; 2) DMF, rt, 48 h
3: 75 percent / methanesulfonic acid / CH2Cl2 / 24 h / Ambient temperature
4: 87 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 - 20 °C
5: 80 percent / iodotrimethylsilane, thiophenol / CH2Cl2 / 24 h / Ambient temperature
6: 89 percent / Et3N / tetrahydrofuran / 1 h / 0 - 20 °C
7: 72 percent / Et3N / acetonitrile / 24 h / Ambient temperature
With
2,6-dimethylpyridine; hydrogenchloride; methanesulfonic acid; trimethylsilyl iodide; sodium hydride; thiophenol; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo9618029