lithium aluminium tetrahydride in tetrahydrofuran; diethyl ether 18 h; Ambient temperature;

1: aq. CrO3, H2SO4 / acetone / 2 h / Ambient temperature 2: 1.) LHMDS / 1.) THF, from -78 deg C to 0 deg C, 2.) THF, -78 deg C 3: 83 percent / n-Bu4NOTf, aq. K2CO3, 14 percent Pd(OAc)2 / dimethylformamide / 14 h / 55 °C 4: 2,6-lutidine / CH2Cl2 / 0.17 h / Ambient temperature 5: MeOH / CH2Cl2 / 0.25 h / Ambient temperature 6: Et3N / CH2Cl2 / 3 h 7: pyridine*HF / 2 h / Ambient temperature 8: 1,3,5-trimethyl-benzene / 3.5 h / 165 °C 9: 63 percent / KF, KHCO3, 30 percent aq. H2O2 / tetrahydrofuran; methanol / 1.5 h / Heating 10: pyridine, DMAP / CH2Cl2 / 0.5 h / Ambient temperature 11: AIBN, tributyltin hydride / benzene / 1 h / Heating 12: 88 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 18 h / Ambient temperature View Scheme

1: 1.) LHMDS / 1.) THF, from -78 deg C to 0 deg C, 2.) THF, -78 deg C 2: 83 percent / n-Bu4NOTf, aq. K2CO3, 14 percent Pd(OAc)2 / dimethylformamide / 14 h / 55 °C 3: 2,6-lutidine / CH2Cl2 / 0.17 h / Ambient temperature 4: MeOH / CH2Cl2 / 0.25 h / Ambient temperature 5: Et3N / CH2Cl2 / 3 h 6: pyridine*HF / 2 h / Ambient temperature 7: 1,3,5-trimethyl-benzene / 3.5 h / 165 °C 8: 63 percent / KF, KHCO3, 30 percent aq. H2O2 / tetrahydrofuran; methanol / 1.5 h / Heating 9: pyridine, DMAP / CH2Cl2 / 0.5 h / Ambient temperature 10: AIBN, tributyltin hydride / benzene / 1 h / Heating 11: 88 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 18 h / Ambient temperature View Scheme

1: 83 percent / n-Bu4NOTf, aq. K2CO3, 14 percent Pd(OAc)2 / dimethylformamide / 14 h / 55 °C 2: 2,6-lutidine / CH2Cl2 / 0.17 h / Ambient temperature 3: MeOH / CH2Cl2 / 0.25 h / Ambient temperature 4: Et3N / CH2Cl2 / 3 h 5: pyridine*HF / 2 h / Ambient temperature 6: 1,3,5-trimethyl-benzene / 3.5 h / 165 °C 7: 63 percent / KF, KHCO3, 30 percent aq. H2O2 / tetrahydrofuran; methanol / 1.5 h / Heating 8: pyridine, DMAP / CH2Cl2 / 0.5 h / Ambient temperature 9: AIBN, tributyltin hydride / benzene / 1 h / Heating 10: 88 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 18 h / Ambient temperature View Scheme

1: 83 percent / n-Bu4NOTf, aq. K2CO3, 14 percent Pd(OAc)2 / dimethylformamide / 14 h / 55 °C 2: 2,6-lutidine / CH2Cl2 / 0.17 h / Ambient temperature 3: MeOH / CH2Cl2 / 0.25 h / Ambient temperature 4: Et3N / CH2Cl2 / 3 h 5: pyridine*HF / 2 h / Ambient temperature 6: 1,3,5-trimethyl-benzene / 3.5 h / 165 °C 7: 63 percent / KF, KHCO3, 30 percent aq. H2O2 / tetrahydrofuran; methanol / 1.5 h / Heating 8: pyridine, DMAP / CH2Cl2 / 0.5 h / Ambient temperature 9: AIBN, tributyltin hydride / benzene / 1 h / Heating 10: 88 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 18 h / Ambient temperature View Scheme

1: Et3N / CH2Cl2 / 3 h 2: pyridine*HF / 2 h / Ambient temperature 3: 1,3,5-trimethyl-benzene / 3.5 h / 165 °C 4: 63 percent / KF, KHCO3, 30 percent aq. H2O2 / tetrahydrofuran; methanol / 1.5 h / Heating 5: pyridine, DMAP / CH2Cl2 / 0.5 h / Ambient temperature 6: AIBN, tributyltin hydride / benzene / 1 h / Heating 7: 88 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 18 h / Ambient temperature View Scheme

1: 2,6-lutidine / CH2Cl2 / 0.17 h / Ambient temperature 2: MeOH / CH2Cl2 / 0.25 h / Ambient temperature 3: Et3N / CH2Cl2 / 3 h 4: pyridine*HF / 2 h / Ambient temperature 5: 1,3,5-trimethyl-benzene / 3.5 h / 165 °C 6: 63 percent / KF, KHCO3, 30 percent aq. H2O2 / tetrahydrofuran; methanol / 1.5 h / Heating 7: pyridine, DMAP / CH2Cl2 / 0.5 h / Ambient temperature 8: AIBN, tributyltin hydride / benzene / 1 h / Heating 9: 88 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 18 h / Ambient temperature View Scheme

1: pyridine, DMAP / CH2Cl2 / 0.5 h / Ambient temperature 2: AIBN, tributyltin hydride / benzene / 1 h / Heating 3: 88 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 18 h / Ambient temperature View Scheme

lithium; ethylenediamine; triethylamine in tetrahydrofuran 3 h;

1: triphenylphosphine; carbon tetrabromide / CH2Cl2 / 3 h / 20 °C 2: triethylamine / 15 h 3: lithium; triethylamine; ethylendiamine / tetrahydrofuran / 3 h View Scheme