Multi-step reaction with 6 steps
1: 100 percent / Na2SO4 / CH2Cl2 / 1 h
2: 1.) LDA / 1.) THF, hexane, -84 deg C, 2 h, 2.) THF, hexane, a) -84 deg C, 2 h, b) from -84 deg C to RT, overnight
3: 90 percent / aq. ammonium cerium(IV) nitrate / acetonitrile / -5 °C
4: N,N-dimethylaminopyridine, Et3N / CH2Cl2 / 2 h / Ambient temperature
5: 1.) LiHMDS / 1.) THF, -45 deg C, 2 min, 2.) THF, -45 deg C, 10 min
6: HF/pyridine / acetonitrile / 1.) 0 deg C, 1 h, 2.) RT, overnight
With
pyridine; dmap; ammonium cerium(IV) nitrate; hydrogen fluoride; sodium sulfate; triethylamine; lithium hexamethyldisilazane; lithium diisopropyl amide;
In
dichloromethane; acetonitrile;
DOI:10.1021/jm960563e