Multi-step reaction with 9 steps
1: 1.) 50 percent NaH / 1.) DMF, 0 deg C, 20 min, 2.) THF, from -83 deg C to -20 deg C, 30 min
2: 94 percent / acetone, p-Ts-OH / 14 h / Ambient temperature
3: 52 percent / DBU / benzene / 6 h
4: 27 percent / DBU / benzene / 3.5 h
5: 2.) 50 percent NaH / 1.) THF, -80 deg C, 20 min, 2.) DMF, THF, from 0 deg C to RT, 1 h
6: 58 percent / 1 N HCl / dimethylsulfoxide; ethanol; H2O / 2 h / Heating
7: 77 percent / Et3N / CH2Cl2 / -20 - 20 °C
8: 1.) SiO2 / 1.) CH2Cl2, -82 deg C, 15 min, 2.) CH2Cl2, RT, 1.5 h
9: 35 percent / Raney Ni / ethanol / 4 h / Heating
With
hydrogenchloride; silica gel; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; acetone;
nickel;
In
ethanol; dichloromethane; water; dimethyl sulfoxide; benzene;