Multi-step reaction with 10 steps
1: 1.) Mg / 1.) THF, reflux, 1 h, 2.) THF, RT, 1 h
2: aq. KOH / ethanol / 3 h / Heating
3: 79 percent / H2 / 10percent Pd/C / acetic acid / 20 h / 60 °C / 3102.9 Torr
4: 83 percent / polyphosphoric ester / CH2Cl2 / 1 h / Heating
5: 1.) sodium borohydride, 2.) 6 M HCl / 1.) 2-propanol, reflux, 1 h, 2.) 2-propanol, reflux, 1 h
6: bromine / CH2Cl2
7: DMF / 1 h / 60 - 70 °C
8: 83 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 2 h
9: 1.) n-BuLi / 1.) ether, hexane, 0 deg C, 15 min, 2.) ether, hexane, RT, 1 h
10: H2 / 10percent Pd/C / ethanol / 2 h / 3102.9 Torr / Ambient temperature
With
hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; polyphosphoric ester; hydrogen; bromine; magnesium; N,N-dimethyl-formamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium on activated charcoal;
In
ethanol; dichloromethane; acetic acid; benzene;
DOI:10.1021/jm980334n