Multi-step reaction with 11 steps
1: conc. sulfuric acid / 1 h / Heating
2: AlCl3 / 1,2-dichloro-ethane / 2.5 h / 15 °C
3: 5N aq. NaOH / methanol / 1 h / 25 °C
4: NaBH4 / methanol / 1 h / 25 - 65 °C
5: 73 percent / KCl / dimethylsulfoxide / 4 h / 170 °C
6: 92 percent / triethylamine / CH2Cl2 / 1 h
7: 1.) NaH / 1.) DMF, a) from 0 deg C - 25 deg C, b) 25 deg C, 30 min, 2.) DMF, 60 deg C, 2 h
8: aq. NaOH / ethanol / 1 h / Heating
9: Et3N / tetrahydrofuran / 0.08 h / -10 °C
10: NaBH4 / tetrahydrofuran; methanol / 0.25 h / 25 °C
11: 100 percent / 0.5 h / 25 °C
With
sodium hydroxide; sodium tetrahydroborate; aluminium trichloride; sulfuric acid; potassium chloride; sodium hydride; triethylamine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane;
DOI:10.1016/S0968-0896(97)00089-8