1: 130 °C 2: benzene; thionyl chloride 3: diethyl ether 4: silver oxide; methanol 5: aqueous HI; acetic acid View Scheme

1.1: triethylamine / dichloromethane / 4 h / |Cooling with ice 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / |Cooling with ice; |Reflux 3.1: triethylamine; 1H-imidazole; thionyl chloride / dichloromethane / |Cooling with ice 3.2: 0 °C 4.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -10 °C / |Inert atmosphere 4.2: -10 - 20 °C / |Inert atmosphere 5.1: hydrogenchloride; water / hexane; tetrahydrofuran 6.1: palladium on activated charcoal; palladium hydroxide on carbon; hydrogen / tetrahydrofuran / 24 h / 20 °C 7.1: toluene / |Reflux 8.1: lithium aluminium tetrahydride / diethyl ether / 4 h / |Cooling with ice; |Reflux 9.1: hydrogenchloride / diethyl ether View Scheme

1.1: triethylamine / dichloromethane / 4 h / |Cooling with ice 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / |Cooling with ice; |Reflux 3.1: triethylamine; 1H-imidazole; thionyl chloride / dichloromethane / |Cooling with ice 3.2: 0 °C 4.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -10 °C / |Inert atmosphere 4.2: -10 - 20 °C / |Inert atmosphere 5.1: hydrogenchloride; water / hexane; tetrahydrofuran 6.1: palladium on activated charcoal; palladium hydroxide on carbon; hydrogen / tetrahydrofuran / 24 h / 20 °C 7.1: toluene / |Reflux 8.1: lithium aluminium tetrahydride / diethyl ether / 4 h / |Cooling with ice; |Reflux 9.1: hydrogenchloride / diethyl ether View Scheme