Multi-step reaction with 11 steps
1: 1.) 60percent NaH / 1.) DMF, 0 deg C, 50 min, 2.) DMF, overnight
2: 18 h / 50 °C
3: K2CO3 / butan-2-one / 4 h / Ambient temperature
4: K2CO3 / butan-2-one / 60 °C
5: aq. KOH / dimethylsulfoxide
6: toluene / 1 h / Heating
7: benzene / 2 h / Ambient temperature
8: tetrahydrofuran / 1 h / 0 °C
9: aq. NH4OH / tetrahydrofuran / 1 h / Ambient temperature
10: H2 / 10percent Pd/C / ethyl acetate
11: K2CO3, KI / dimethylformamide / 5 h
With
potassium hydroxide; ammonium hydroxide; hydrogen; sodium hydride; potassium carbonate; potassium iodide;
palladium on activated charcoal;
In
tetrahydrofuran; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; butanone; benzene;
DOI:10.1021/jm960395q