lithium aluminium tetrahydride in tetrahydrofuran 1.25 h; Heating;

4 A molecular sieve in tetrahydrofuran 14 h; Ambient temperature;

1: 87 percent / CH2Cl2 2: 80 percent / P2O5 / benzene / 30 - 35 °C 3: 70 percent / LiAlH4 / tetrahydrofuran / 1.25 h / Heating View Scheme

1: 80 percent / P2O5 / benzene / 30 - 35 °C 2: 70 percent / LiAlH4 / tetrahydrofuran / 1.25 h / Heating View Scheme

1: pyridinium chlorochromate 2: p-toluenesulfonic acid / benzene 4: tetra-n-butylammonium fluoride 5: 1.) d.HCl; 2.) triphenylphosphorane / 1.) in acetone; 2.) Wittig-reaction View Scheme

1: p-toluenesulfonic acid / benzene 3: tetra-n-butylammonium fluoride 4: 1.) d.HCl; 2.) triphenylphosphorane / 1.) in acetone; 2.) Wittig-reaction View Scheme

1: 51 percent / triphenylphosphane, CCl4 / 48 h / Heating 2: 88 percent / p-toluenesulfonic acid / 1 h / 80 - 90 °C 3: 90 percent / NaBH4/H2O / tetrahydrofuran; 2-methoxy-ethanol / 24 h / Ambient temperature 4: 88 percent / pyridine / 12 h / Ambient temperature 5: N-bromosuccinimide, dibenzoylperoxide / CCl4 / 0.17 h / 80 °C / Irradiation 6: 1) trimethylphosphite / 1) 90 min, 125 deg C, xylol; 2) CH2Cl2 7: 95 percent / Na / methanol / 2 h / Heating 8: 90 percent / imidazole / dimethylformamide / 12 h / Ambient temperature 9: 69 percent / NaHCO3 / dimethylsulfoxide / 0.25 h / 150 °C 10: 71 percent / THF / acetone / Heating 11: 91 percent / Na / methanol / 2 h / Heating 12: 71 percent / pyridine / 12 h / 0 °C 13: 66 percent / NaHCO3 / dimethylsulfoxide / 0.25 h / 150 °C 14: 73 percent / tetrahydrofuran / 12 h / Ambient temperature 15: 81 percent / 40 percent HF / acetonitrile / 1 h / Ambient temperature 16: 44 percent / imidazole / dimethylformamide / 12 h / Ambient temperature 17: 44 percent / tetrahydrofuran / 12 h / Ambient temperature 18: 61 percent / 40 percent HF / acetonitrile / 1 h / Ambient temperature 19: 32 percent / molecular sieve (4 Angstroem) / tetrahydrofuran / 14 h / Ambient temperature View Scheme

1: 44 percent / imidazole / dimethylformamide / 12 h / Ambient temperature 2: 44 percent / tetrahydrofuran / 12 h / Ambient temperature 3: 61 percent / 40 percent HF / acetonitrile / 1 h / Ambient temperature 4: 32 percent / molecular sieve (4 Angstroem) / tetrahydrofuran / 14 h / Ambient temperature View Scheme

1: 88 percent / pyridine / 12 h / Ambient temperature 2: N-bromosuccinimide, dibenzoylperoxide / CCl4 / 0.17 h / 80 °C / Irradiation 3: 1) trimethylphosphite / 1) 90 min, 125 deg C, xylol; 2) CH2Cl2 4: 95 percent / Na / methanol / 2 h / Heating 5: 90 percent / imidazole / dimethylformamide / 12 h / Ambient temperature 6: 69 percent / NaHCO3 / dimethylsulfoxide / 0.25 h / 150 °C 7: 71 percent / THF / acetone / Heating 8: 91 percent / Na / methanol / 2 h / Heating 9: 71 percent / pyridine / 12 h / 0 °C 10: 66 percent / NaHCO3 / dimethylsulfoxide / 0.25 h / 150 °C 11: 73 percent / tetrahydrofuran / 12 h / Ambient temperature 12: 81 percent / 40 percent HF / acetonitrile / 1 h / Ambient temperature 13: 44 percent / imidazole / dimethylformamide / 12 h / Ambient temperature 14: 44 percent / tetrahydrofuran / 12 h / Ambient temperature 15: 61 percent / 40 percent HF / acetonitrile / 1 h / Ambient temperature 16: 32 percent / molecular sieve (4 Angstroem) / tetrahydrofuran / 14 h / Ambient temperature View Scheme

1: 88 percent / p-toluenesulfonic acid / 1 h / 80 - 90 °C 2: 90 percent / NaBH4/H2O / tetrahydrofuran; 2-methoxy-ethanol / 24 h / Ambient temperature 3: 88 percent / pyridine / 12 h / Ambient temperature 4: N-bromosuccinimide, dibenzoylperoxide / CCl4 / 0.17 h / 80 °C / Irradiation 5: 1) trimethylphosphite / 1) 90 min, 125 deg C, xylol; 2) CH2Cl2 6: 95 percent / Na / methanol / 2 h / Heating 7: 90 percent / imidazole / dimethylformamide / 12 h / Ambient temperature 8: 69 percent / NaHCO3 / dimethylsulfoxide / 0.25 h / 150 °C 9: 71 percent / THF / acetone / Heating 10: 91 percent / Na / methanol / 2 h / Heating 11: 71 percent / pyridine / 12 h / 0 °C 12: 66 percent / NaHCO3 / dimethylsulfoxide / 0.25 h / 150 °C 13: 73 percent / tetrahydrofuran / 12 h / Ambient temperature 14: 81 percent / 40 percent HF / acetonitrile / 1 h / Ambient temperature 15: 44 percent / imidazole / dimethylformamide / 12 h / Ambient temperature 16: 44 percent / tetrahydrofuran / 12 h / Ambient temperature 17: 61 percent / 40 percent HF / acetonitrile / 1 h / Ambient temperature 18: 32 percent / molecular sieve (4 Angstroem) / tetrahydrofuran / 14 h / Ambient temperature View Scheme