Multi-step reaction with 8 steps
1: 95 percent / pyridine / 12 h / Ambient temperature
2: 65 percent / gaseous HCl / acetone; H2O / 12 h
3: 1.) 2.34M n-BuLi / 1.) ice-cooling, 30 min, THF; 2.) THF, 2h, 5 deg C to 10 deg C, then 8.5h, RT
4: NaOMe / methanol / 12 h / Ambient temperature
5: 68 percent / pyridine / 48 h / Ambient temperature
6: CrO3-pyridine / CH2Cl2 / 0.5 h / Ambient temperature
7: 72 percent / 1,5-diazabicyclo<5,4,0>undecene-5 (DBU) / benzene / 5 h / 25 °C
8: 97 percent / p-toluenesulfonic acid / methanol / 5 h / 25 °C
With
hydrogenchloride; n-butyllithium; chromium trioxide-pyridine complex; sodium methylate; toluene-4-sulfonic acid; 1,5-Diazabicyclo[5.4.0]undec-5-ene;
In
pyridine; methanol; dichloromethane; water; acetone; benzene;
DOI:10.1016/S0040-4020(01)83120-3