lithium aluminium tetrahydride in diethyl ether

1: 82 percent / K2CO3 / acetone / 3 h / Heating 2: 86 percent / LiAlH4 / diethyl ether View Scheme

1.1: potassium hydroxide; hydrogenchloride / water / 24 h / |Inert atmosphere 1.2: 0.67 h / |Inert atmosphere; |Cooling with ice 2.1: 1H-imidazole / dichloromethane / 1.5 h / |Inert atmosphere; |Cooling with ice View Scheme

1.1: sulfuric acid / 22 h / 75 °C / |Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.67 h / |Inert atmosphere; |Cooling with ice 2.2: 2.83 h / |Inert atmosphere 3.1: potassium hydroxide; hydrogenchloride / water / 24 h / |Inert atmosphere 3.2: 0.67 h / |Inert atmosphere; |Cooling with ice 4.1: 1H-imidazole / dichloromethane / 1.5 h / |Inert atmosphere; |Cooling with ice View Scheme

1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.67 h / |Inert atmosphere; |Cooling with ice 1.2: 2.83 h / |Inert atmosphere 2.1: potassium hydroxide; hydrogenchloride / water / 24 h / |Inert atmosphere 2.2: 0.67 h / |Inert atmosphere; |Cooling with ice 3.1: 1H-imidazole / dichloromethane / 1.5 h / |Inert atmosphere; |Cooling with ice View Scheme

1H-imidazole in dichloromethane 1.5 h; Inert atmosphereCooling with ice;

1: PBr3 / benzene 2: Na / tetrahydrofuran 3: CrO3, aq. H2SO4 / acetone View Scheme

manganese(IV) oxide in tetrahydrofuran