Multi-step reaction with 11 steps
1: 94 percent / 1) NaH / dimethylformamide / 1) 2 h, 0 deg C, 2) 5 h, room temp.
2: 81 percent / 98percent acetic acid / 30 °C
3: 91 percent / 1) NaH / dimethylformamide / 1) 2 h, 0 deg C, 2) 5 h, room temp.
4: 91 percent / acetic acid / tetrahydrofuran; H2O / 60 °C
5: p-toluenesulfonic acid / toluene / 0.17 h / Ambient temperature
6: 90percent acetic acid / toluene / 0.08 h
7: 89 percent / ethyldiisopropylamine / CH2Cl2
8: 1 N NaOCH3 / methanol
9: 91 percent / 1) NaH / dimethylformamide / 1) 2 h, 0 deg C, 2) 5 h, room temp.
10: 95 percent / 3 N HCl / tetrahydrofuran / 10 h / 60 °C
11: 89 percent / pyridine / CH2Cl2 / -40 °C
With
pyridine; hydrogenchloride; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;