Multi-step reaction with 14 steps
1: 4percent aq. NaOH, 6percent aq. H2O2 / methanol / 2 h / 50 °C
2: pyridine
3: 77 percent / K2CO3 / acetone; dimethylformamide / 50 h / Heating
4: 10percent aq. NaOH / methanol / 0.5 h / Ambient temperature
5: K2CO3 / acetone / 3 h / Heating
6: H2 / 10percent Pd/C / methanol; ethyl acetate / Ambient temperature
7: pyridine
8: 1.) AcOH, BF3(g), 2.) pyridine / 1.) from 50 to 60 deg C, 5 h
9: 10percent aq. NaOH / methanol / 0.25 h / Ambient temperature
10: (i-Pr)2NEt / CH2Cl2 / 0.83 h / 5 °C
11: pyridine / 3 h / 60 - 70 °C
12: KOH, pyridine / 2 h / 60 °C
13: conc. H2SO4, HOAc / 1 h / 50 °C
14: 98 percent / K2CO3 / dimethylformamide / 0.08 h / 150 °C
With
pyridine; potassium hydroxide; sodium hydroxide; sulfuric acid; boron trifluoride; hydrogen; dihydrogen peroxide; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine;
palladium on activated charcoal;
In
methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1246/bcsj.69.1033