1: ethanolic KOH-solution 2: phosphorus (V)-chloride View Scheme

sodium hydroxide

1.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 1.2: 50 - 60 °C 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C View Scheme

1.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 1.2: 50 - 60 °C 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 5.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction View Scheme

1.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 1.2: 50 - 60 °C 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 4.2: 0 °C / Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C View Scheme

1.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 1.2: 50 - 60 °C 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 4.2: 0 °C / Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C View Scheme

sodium bis(2-methoxyethoxy)aluminium dihydride in toluene 2 h; Heating;

Multi-step reaction with 2 steps 1: 41 percent / Vitride / toluene / 2 h / Heating2: PBr3 / toluene / 0.17 h / 100 °C  

Multi-step reaction with 5 steps 1.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C1.2: 50 - 60 °C2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C3.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction4.2: 0 °C / Large scale reaction5.1: N-bromosuccinmide / N,N-dimethyl-formamide / 0.5 h / 20 °C