hydrogenchloride; sodium chloride; potassium carbonate in 1,4-dioxane; ethanol

triethylsilane in trifluoroacetic acid 2 h; Heating;

thionyl chloride 5 h; Heating;

in tetrahydrofuran

1: 100 percent / KOH / dimethylsulfoxide; H2O / Ambient temperature 2: 52 percent / Et3N / CH2Cl2 / 2.75 h / 0 - 20 °C 4: 1.) 4-(dimethylamino)pyridine 6: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C 7: 100 percent / 6 N HCl / 3 h / Heating View Scheme

1: 100 percent / KOH / dimethylsulfoxide; H2O / Ambient temperature 2: 52 percent / Et3N / CH2Cl2 / 2.75 h / 0 - 20 °C 4: 1.) 4-(dimethylamino)pyridine 6: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C 7: 100 percent / 6 N HCl / 3 h / Heating 8: 27 percent / LiAlH4 / diethyl ether View Scheme

potassium hydroxide in water; dimethyl sulfoxide Ambient temperature;