Multi-step reaction with 6 steps
1.1: n-BuLi / toluene; hexane / 0.5 h / -78 °C
1.2: 70 percent / toluene; hexane / 0.67 h
2.1: NaH / dimethylformamide / 1.25 h / 0 - 20 °C
2.2: 97 percent / dimethylformamide / 20 h / 20 °C
3.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -100 °C
3.2: 100 percent / tetrahydrofuran; hexane / 0.17 h / -100 - -78 °C
4.1: 88 percent / SOCl2; pyridine / toluene / 1 h / 20 °C
5.1: KHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide; toluene / 0.5 h
5.2: tetrahydrofuran; toluene; hexamethylphosphoric acid triamide / 15 h / 20 °C
6.1: aq. LiOH / tetrahydrofuran; methanol / 2 h / 60 °C
6.2: 710 mg / aq. HCl / tetrahydrofuran; methanol / 20 °C
With
pyridine; lithium hydroxide; n-butyllithium; thionyl chloride; potassium hexamethylsilazane; sodium hydride;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm0204542