hydrogenchloride in tetrahydrofuran 48 h; Ambient temperature;

1: 87 percent / hexadecyltributylphosphonium bromide; HBr / 7.5 h / Heating 2: 88 percent / LiAlH4 / tetrahydrofuran / 2.5 h / 67 °C 3: 33 percent / trifluoroacetic acid / 2.75 h / Heating View Scheme

1: 88 percent / LiAlH4 / tetrahydrofuran / 2.5 h / 67 °C 2: 33 percent / trifluoroacetic acid / 2.75 h / Heating View Scheme

trifluoroacetic acid 2.75 h; Heating;

1: 88 percent / CH2Cl2 / Ambient temperature; overnight 2: 1) SnCl4, triethylamine / 1) toluene, CH2Cl2, 20 min, room temperature 2) 100 deg C, 8 h 3: 90 percent / 4 M hydrochloric acid / tetrahydrofuran / 48 h / Ambient temperature View Scheme

1: 1) SnCl4, triethylamine / 1) toluene, CH2Cl2, 20 min, room temperature 2) 100 deg C, 8 h 2: 90 percent / 4 M hydrochloric acid / tetrahydrofuran / 48 h / Ambient temperature View Scheme