Multi-step reaction with 7 steps
1.1: n-butyllithium; N,N',N'-trimethylenediamine / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: 10 h / -40 °C / Inert atmosphere
1.3: Inert atmosphere
2.1: potassium hydroxide / methanol; N,N-dimethyl-formamide / 2 h / -10 °C / Inert atmosphere
2.2: 0.5 h / -10 °C / Inert atmosphere
3.1: sodium hydroxide; sodium tetrahydroborate; diphenyl diselenide / ethanol / 20 - 40 °C / Inert atmosphere
4.1: bromic acid / water / 5 h / 105 °C
5.1: sodium iodide; potassium hydroxide / ethanol / 20 °C
6.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 3 h
7.1: sodium hydroxide / chloroform; water / 16 h / 20 °C / Cooling with ice
With
sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; diphenyl diselenide; bromic acid; N,N',N'-trimethylenediamine; N,N-dimethyl-formamide; sodium iodide; potassium hydroxide; sodium hydroxide;
In
tetrahydrofuran; methanol; ethanol; chloroform; water; N,N-dimethyl-formamide; toluene;
DOI:10.1002/chem.201201895