Multi-step reaction with 10 steps
1.1: 1H-imidazole / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere
2.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 °C / Inert atmosphere
2.2: 1.5 h / -78 - 20 °C / Inert atmosphere
3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / diethyl ether; toluene / 4 h / 0 - 20 °C / Inert atmosphere
4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 20 °C / Inert atmosphere
5.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
5.2: 3.5 h / -78 - -20 °C / Inert atmosphere
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere
7.1: 1H-imidazole; dmap / dichloromethane / 1 h / 0 °C
8.1: water; hydrogenchloride / tetrahydrofuran / 1 h / 20 °C
9.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1.5 h / 0 °C
10.1: hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / ethanol; water / 12 h / 0 - 20 °C / Inert atmosphere
With
1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; n-butyllithium; hexaammonium heptamolybdate tetrahydrate; water; dihydrogen peroxide; iodine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; diethylazodicarboxylate;
In
tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; toluene;
5.1: |Evans Aldol Reaction / 5.2: |Evans Aldol Reaction / 9.1: |Mitsunobu Displacement;
DOI:10.1002/chem.201501304