Multi-step reaction with 10 steps
1: 1.) Mg, 2.) dilithium tetrachlorocopper(II) / 1.) THF, reflux, 2 h, 2.) a) THF, reflux, 2 h, b) THF, RT, 16 h
2: 96 percent / BBr3 / CH2Cl2 / 3 h / Ambient temperature
3: 1.) NaH / 1.) DMF, reflux, 2 h, 2.) DMF, reflux, 24 h
4: 61 percent / 1N aq. HCl / methanol / 3 h / Heating
5: 97 percent / pyridine / 48 h / Ambient temperature
6: 73 percent / NaH / dimethylformamide / 3 h / Ambient temperature
7: 33 percent / p-TsOH / methanol; tetrahydrofuran / 24 h / Ambient temperature
8: 1.) Et3N, 2.) 0.5 M aq. AcONa / 1.) CCl4, 2 h, 2.) THF
9: 1.) water, DMF, 2.) silver carbonate / 1.) chloroform, 2-propanol, 65 deg C, 5 h, 2.) ethanol, water, RT, 1 h
10: 94 percent / H2 / 5percent Pd/C / methanol; acetic acid / 18 h
With
pyridine; hydrogenchloride; dilithium tetrachlorocuprate; water; hydrogen; sodium acetate; boron tribromide; sodium hydride; toluene-4-sulfonic acid; magnesium; triethylamine; N,N-dimethyl-formamide; silver carbonate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jm00375a016