hydrogenchloride in acetone 3 h; Heating;

boron trifluoride diethyl etherate; water in acetone 10 h; Ambient temperature;

1: H2 / Pd/BaSO4 / methanol; pyridine / 1 h 2: 71 percent / 3.0 M hydrochloric acid / acetone / 3 h / Heating View Scheme

1: 63 percent / NaNO2 / dimethylformamide / 7 h / Ambient temperature 2: 74 percent / Amberlist A-21 / 16 h / Ambient temperature 3: 76 percent / pyridinium chlorochromate, 3 A molecular sieves / CH2Cl2 / 24 h / Ambient temperature 4: 97 percent / methanol / 10 h / Ambient temperature 5: 95 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 6: 76 percent / BF3*(C2H5)2O, H2O / acetone / 10 h / Ambient temperature View Scheme

1: 74 percent / Amberlist A-21 / 16 h / Ambient temperature 2: 76 percent / pyridinium chlorochromate, 3 A molecular sieves / CH2Cl2 / 24 h / Ambient temperature 3: 97 percent / methanol / 10 h / Ambient temperature 4: 95 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 5: 76 percent / BF3*(C2H5)2O, H2O / acetone / 10 h / Ambient temperature View Scheme

1: 76 percent / pyridinium chlorochromate, 3 A molecular sieves / CH2Cl2 / 24 h / Ambient temperature 2: 97 percent / methanol / 10 h / Ambient temperature 3: 95 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 4: 76 percent / BF3*(C2H5)2O, H2O / acetone / 10 h / Ambient temperature View Scheme

1: 97 percent / methanol / 10 h / Ambient temperature 2: 95 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 3: 76 percent / BF3*(C2H5)2O, H2O / acetone / 10 h / Ambient temperature View Scheme

1: 95 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 2: 76 percent / BF3*(C2H5)2O, H2O / acetone / 10 h / Ambient temperature View Scheme

diethyl ether T=-78°C;

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