Multi-step reaction with 6 steps
1: 1) 1.56 M nBuLi in hexane / 1) THF, -40 deg C then 0 deg C, 40 min, 2) THF, HMPA, 0 deg C, 1 h then 1 h, RT
2: 96 percent / hydrogen / 10percent Pd/C / ethyl acetate / 12 h / Ambient temperature
3: pyridine / ) deg C, 1 h; RT, 5 h
4: 91 percent / NaI, NaHCO3 / acetone / 8 h
5: 10 0.6 m NaHMDS in toluene / 1) THF, 0 deg C, 30 min, 2) THF, toluene, HMPA, 0 deg C to RT
6: 99 percent / p-TsOH / methanol / 48 h
With
pyridine; n-butyllithium; hydrogen; sodium hexamethyldisilazane; sodium hydrogencarbonate; toluene-4-sulfonic acid; sodium iodide;
palladium on activated charcoal;
In
methanol; ethyl acetate; acetone;