hydrogenchloride 15 h; Heating;

1: 1.) LDA / 1.) THF, -60 deg C, 2.) THF, r.t. 2: 85 percent / tetrahydrofuran / 0.5 h / Ambient temperature 3: 85 percent / DDQ, CSA / benzene / 5 h / Heating 4: 87 percent / 1N HCl / 12 h / Heating View Scheme

1: 85 percent / tetrahydrofuran / 0.5 h / Ambient temperature 2: 85 percent / DDQ, CSA / benzene / 5 h / Heating 3: 87 percent / 1N HCl / 12 h / Heating View Scheme

1: 57 percent / n-BuLi / tetrahydrofuran / 0.05 h / 0 °C 2: 98 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 3: 95 percent / DMSO, Et3N / CH2Cl2 / -60 deg C then warming up to 0 deg C 4: DIBAL / toluene / 0.33 h / -78 °C 5: 90 percent / (i-Pr)2NEt / tetrahydrofuran / 3 h / Heating 6: 94 percent / LiAlH4 / diethyl ether / 1 h / Heating 7: 72 percent / CAN / ethanol; H2O / -40 - 0 °C 8: Na2S2O4 / CHCl3; H2O / Ambient temperature 9: Me3SiBr / CH2Cl2 / 0.17 h / Heating 10: AcOK / ethanol / 0.33 h / Ambient temperature 12: 85 percent / tetrahydrofuran / 0.5 h / Ambient temperature 13: 85 percent / DDQ, CSA / benzene / 5 h / Heating 14: 87 percent / 1N HCl / 12 h / Heating View Scheme

1: 57 percent / n-BuLi / tetrahydrofuran / 0.05 h / 0 °C 2: 98 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 3: 95 percent / DMSO, Et3N / CH2Cl2 / -60 deg C then warming up to 0 deg C 4: DIBAL / toluene / 0.33 h / -78 °C 5: 90 percent / (i-Pr)2NEt / tetrahydrofuran / 3 h / Heating 6: 94 percent / LiAlH4 / diethyl ether / 1 h / Heating 7: 72 percent / CAN / ethanol; H2O / -40 - 0 °C 8: Na2S2O4 / CHCl3; H2O / Ambient temperature 9: Me3SiBr / CH2Cl2 / 0.17 h / Heating 10: AcOK / ethanol / 0.33 h / Ambient temperature 12: 85 percent / tetrahydrofuran / 0.5 h / Ambient temperature 13: 85 percent / DDQ, CSA / benzene / 5 h / Heating 14: 87 percent / 1N HCl / 12 h / Heating View Scheme

1: 98 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 2: 95 percent / DMSO, Et3N / CH2Cl2 / -60 deg C then warming up to 0 deg C 3: DIBAL / toluene / 0.33 h / -78 °C 4: 90 percent / (i-Pr)2NEt / tetrahydrofuran / 3 h / Heating 5: 94 percent / LiAlH4 / diethyl ether / 1 h / Heating 6: 72 percent / CAN / ethanol; H2O / -40 - 0 °C 7: Na2S2O4 / CHCl3; H2O / Ambient temperature 8: Me3SiBr / CH2Cl2 / 0.17 h / Heating 9: AcOK / ethanol / 0.33 h / Ambient temperature 11: 85 percent / tetrahydrofuran / 0.5 h / Ambient temperature 12: 85 percent / DDQ, CSA / benzene / 5 h / Heating 13: 87 percent / 1N HCl / 12 h / Heating View Scheme

1: 95 percent / DMSO, Et3N / CH2Cl2 / -60 deg C then warming up to 0 deg C 2: DIBAL / toluene / 0.33 h / -78 °C 3: 90 percent / (i-Pr)2NEt / tetrahydrofuran / 3 h / Heating 4: 94 percent / LiAlH4 / diethyl ether / 1 h / Heating 5: 72 percent / CAN / ethanol; H2O / -40 - 0 °C 6: Na2S2O4 / CHCl3; H2O / Ambient temperature 7: Me3SiBr / CH2Cl2 / 0.17 h / Heating 8: AcOK / ethanol / 0.33 h / Ambient temperature 10: 85 percent / tetrahydrofuran / 0.5 h / Ambient temperature 11: 85 percent / DDQ, CSA / benzene / 5 h / Heating 12: 87 percent / 1N HCl / 12 h / Heating View Scheme

1: DIBAL / toluene / 0.33 h / -78 °C 2: 90 percent / (i-Pr)2NEt / tetrahydrofuran / 3 h / Heating 3: 94 percent / LiAlH4 / diethyl ether / 1 h / Heating 4: 72 percent / CAN / ethanol; H2O / -40 - 0 °C 5: Na2S2O4 / CHCl3; H2O / Ambient temperature 6: Me3SiBr / CH2Cl2 / 0.17 h / Heating 7: AcOK / ethanol / 0.33 h / Ambient temperature 9: 85 percent / tetrahydrofuran / 0.5 h / Ambient temperature 10: 85 percent / DDQ, CSA / benzene / 5 h / Heating 11: 87 percent / 1N HCl / 12 h / Heating View Scheme

1: 85 percent / tetrahydrofuran / 0.5 h / Ambient temperature 2: 85 percent / DDQ, CSA / benzene / 5 h / Heating 3: 87 percent / 1N HCl / 12 h / Heating View Scheme

1: 94 percent / LiAlH4 / diethyl ether / 1 h / Heating 2: 72 percent / CAN / ethanol; H2O / -40 - 0 °C 3: Na2S2O4 / CHCl3; H2O / Ambient temperature 4: Me3SiBr / CH2Cl2 / 0.17 h / Heating 5: AcOK / ethanol / 0.33 h / Ambient temperature 7: 85 percent / tetrahydrofuran / 0.5 h / Ambient temperature 8: 85 percent / DDQ, CSA / benzene / 5 h / Heating 9: 87 percent / 1N HCl / 12 h / Heating View Scheme