Multi-step reaction with 10 steps
1: SOCl2, DMF / CH2Cl2 / 4 h / Heating
2: conc. NH4OH / tetrahydrofuran / 0 °C
3: 1) Br2, aq. NaOH / 1) reflux, 2 h, 2) reflux, 2 h
4: LiAlH4 / diethyl ether / 3.5 h / Heating
5: K2CO3, KI / dimethylformamide / 100 °C
6: 88 percent / 1.6 M nBuLi / tetrahydrofuran; hexane / 1.5 h / -80 °C
7: NH4OAc / ethanol / 5 h / Heating
8: LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating
9: aq. NaOH / toluene / 1 h / 0 °C
10: K2CO3, KI / dimethylformamide / 5 h / 100 °C
With
ammonium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; ammonium acetate; bromine; potassium carbonate; N,N-dimethyl-formamide; potassium iodide;
In
tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0223-5234(99)80047-6