Multi-step reaction with 9 steps
1.1: magnesium / ethylene dibromide; tetrahydrofuran / 1 h / Inert atmosphere; Reflux
1.2: 5 h / -78 °C / Inert atmosphere
2.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
3.1: hydrogenchloride / isopropyl alcohol; water / 2 h / 0 - 20 °C / Inert atmosphere
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C / Inert atmosphere
4.2: 2 h / -78 - 20 °C / Inert atmosphere
5.1: magnesium; isopropyl chloride / ethylene dibromide; tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
5.2: 1.5 h / -78 °C / Inert atmosphere
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
6.2: 2 h / -78 - 20 °C / Inert atmosphere
7.1: sodium dihydrogen phosphate monohydrate; sodium chlorite / water; tert-butyl alcohol / 0 - 20 °C / Inert atmosphere
8.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
8.2: 2 h / 20 °C / Inert atmosphere
9.1: diethyl ether / 36 h / 0 - 20 °C / Inert atmosphere
With
1H-imidazole; hydrogenchloride; sodium chlorite; sodium dihydrogen phosphate monohydrate; oxalyl dichloride; isopropyl chloride; sodium hydride; magnesium; dimethyl sulfoxide;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; ethylene dibromide; N,N-dimethyl-formamide; isopropyl alcohol; tert-butyl alcohol;
4.1: |Swern Oxidation / 6.1: |Swern Oxidation;
DOI:10.1002/asia.201403325