Multi-step reaction with 9 steps
1: 93 percent / BBr3 / CH2Cl2 / 4 h
2: 93 percent / p-toluenesulfonic acid (p-TSA) / benzene / 4 h / Heating
3: 1.) NaH / 1.) DMF, C6H6, a) RT, 15 min, b) reflux, 1 h, 2.) DMF, C6H6, reflux, 4 h
4: 98 percent / NaOH / ethane-1,2-diol / 18 h / Heating
5: 82 percent / Et3N, (C6H5O)2PON3 / various solvent(s) / 1 h / 90 °C
6: 71 percent / LiAlH4 / tetrahydrofuran / 5 h / Heating
7: Et3N / tetrahydrofuran / 7 h / 0 °C
8: LiAlH4 / tetrahydrofuran / 7 h / Heating
9: H2, 2 N etheral HCl / 10percent Pd/C / ethyl acetate / 24 h
With
hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; diphenyl phosphoryl azide; hydrogen; boron tribromide; sodium hydride; toluene-4-sulfonic acid; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; ethylene glycol; ethyl acetate; benzene;
DOI:10.1021/jm00135a019