1: 4-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-ol With pyridine; thionyl chloride in dichloromethane T=0 - 20°C; 2: ethanolamine With N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide T=50°C; 48 h; Product distribution / selectivity;

1.1: ethanol; silica gel; sodium tetrahydroborate / 0 - 20 °C 2.1: potassium carbonate; hydroxylamine hydrochloride / ethanol / 16 h / Reflux 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.33 h / 20 °C 3.2: 1.08 h / 20 - 130 °C / Microwave irradiation 4.1: thionyl chloride; pyridine / dichloromethane / 0 - 20 °C 4.2: 48 h / 50 °C View Scheme

1.1: potassium carbonate; hydroxylamine hydrochloride / ethanol / 16 h / Reflux 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.33 h / 20 °C 2.2: 1.08 h / 20 - 130 °C / Microwave irradiation 3.1: thionyl chloride; pyridine / dichloromethane / 0 - 20 °C 3.2: 48 h / 50 °C View Scheme

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.33 h / 20 °C 1.2: 1.08 h / 20 - 130 °C / Microwave irradiation 2.1: thionyl chloride; pyridine / dichloromethane / 0 - 20 °C 2.2: 48 h / 50 °C View Scheme