hydrogenchloride in diethyl ether; isopropyl alcohol 16 h; Ambient temperature;

1: 1.) LiAlH4, 2.) PBr3 2: 1.) n-butyllithium, tetramethylethylenediamine, 2.) CuI / 1.) THF-hexane, room temperature, 2 h; 2.) -78 -> -40 deg C, 90 min, 3.) room temperature, 16 h 3: 1.) n-butyllithium, tetramethylethylenediamine / 1.) hexane, room temperature, 3 h, 2.) -78 deg C -> room temperature (16 h) 4: 92 percent / 4N hydrochloric acid / propan-2-ol; diethyl ether / 16 h / Ambient temperature View Scheme

1: 1) K2CO3, 2) 18-crown-6 / 1) acetonitrile, 0 deg C, 15 min; 2) room temperature, 10 h 2: 1.) n-butyllithium, tetramethylethylenediamine, 2.) CuI / 1.) THF-hexane, room temperature, 2 h; 2.) -78 -> -40 deg C, 90 min, 3.) room temperature, 16 h 3: 1.) n-butyllithium, tetramethylethylenediamine / 1.) hexane, room temperature, 3 h, 2.) -78 deg C -> room temperature (16 h) 4: 92 percent / 4N hydrochloric acid / propan-2-ol; diethyl ether / 16 h / Ambient temperature View Scheme

1: 1.) LiAlH4, 2.) PBr3 2: 1.) n-butyllithium, tetramethylethylenediamine, 2.) CuI / 1.) THF-hexane, room temperature, 2 h; 2.) -78 -> -40 deg C, 90 min, 3.) room temperature, 16 h 3: 1.) n-butyllithium, tetramethylethylenediamine / 1.) hexane, room temperature, 3 h, 2.) -78 deg C -> room temperature (16 h) 4: 92 percent / 4N hydrochloric acid / propan-2-ol; diethyl ether / 16 h / Ambient temperature View Scheme

1: 1.) n-butyllithium, tetramethylethylenediamine, 2.) CuI / 1.) THF-hexane, room temperature, 2 h; 2.) -78 -> -40 deg C, 90 min, 3.) room temperature, 16 h 2: 1.) n-butyllithium, tetramethylethylenediamine / 1.) hexane, room temperature, 3 h, 2.) -78 deg C -> room temperature (16 h) 3: 92 percent / 4N hydrochloric acid / propan-2-ol; diethyl ether / 16 h / Ambient temperature View Scheme

1: 1.) n-butyllithium, tetramethylethylenediamine, 2.) CuI / 1.) THF-hexane, room temperature, 2 h; 2.) -78 -> -40 deg C, 90 min, 3.) room temperature, 16 h 2: 1.) n-butyllithium, tetramethylethylenediamine / 1.) hexane, room temperature, 3 h, 2.) -78 deg C -> room temperature (16 h) 3: 92 percent / 4N hydrochloric acid / propan-2-ol; diethyl ether / 16 h / Ambient temperature View Scheme

1: 2.) POCl3, 3.) H2SO4 2: 1.) LiAlH4, 2.) PBr3 3: 1.) n-butyllithium, tetramethylethylenediamine, 2.) CuI / 1.) THF-hexane, room temperature, 2 h; 2.) -78 -> -40 deg C, 90 min, 3.) room temperature, 16 h 4: 1.) n-butyllithium, tetramethylethylenediamine / 1.) hexane, room temperature, 3 h, 2.) -78 deg C -> room temperature (16 h) 5: 92 percent / 4N hydrochloric acid / propan-2-ol; diethyl ether / 16 h / Ambient temperature View Scheme

1: 1.) n-butyllithium, tetramethylethylenediamine / 1.) hexane, room temperature, 3 h, 2.) -78 deg C -> room temperature (16 h) 2: 92 percent / 4N hydrochloric acid / propan-2-ol; diethyl ether / 16 h / Ambient temperature View Scheme