sodium hydroxide in tetrahydrofuran; water T=23°C; 7 h;

lithium hydroxide in ethylene glycol dimethyl ether; water Ambient temperature;

1: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 2.5 h / -78 - 20 °C 2: NaHCO3 / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / Ambient temperature 3: 68 percent / AlH3*Et2O / tetrahydrofuran / 0.5 h / 0 °C 4: 85 percent / Et3N / CH2Cl2 / 0 °C 5: aq. TFA / tetrahydrofuran / Ambient temperature 6: Na2CO3, Pb(OAc)4 / CH2Cl2 / 0.25 h / -78 °C 7: toluene / 3 h / 80 °C 8: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 - 0 °C 9: NaHCO3 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / Ambient temperature 10: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 11: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme

1: 85 percent / Et3N / CH2Cl2 / 0 °C 2: aq. TFA / tetrahydrofuran / Ambient temperature 3: Na2CO3, Pb(OAc)4 / CH2Cl2 / 0.25 h / -78 °C 4: toluene / 3 h / 80 °C 5: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 - 0 °C 6: NaHCO3 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / Ambient temperature 7: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 8: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme

1: toluene / 3 h / 80 °C 2: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 - 0 °C 3: NaHCO3 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / Ambient temperature 4: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 5: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme

1: NaHCO3 / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / Ambient temperature 2: 68 percent / AlH3*Et2O / tetrahydrofuran / 0.5 h / 0 °C 3: 85 percent / Et3N / CH2Cl2 / 0 °C 4: aq. TFA / tetrahydrofuran / Ambient temperature 5: Na2CO3, Pb(OAc)4 / CH2Cl2 / 0.25 h / -78 °C 6: toluene / 3 h / 80 °C 7: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 - 0 °C 8: NaHCO3 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / Ambient temperature 9: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 10: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme

1: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 - 0 °C 2: NaHCO3 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / Ambient temperature 3: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 4: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme

1: 68 percent / AlH3*Et2O / tetrahydrofuran / 0.5 h / 0 °C 2: 85 percent / Et3N / CH2Cl2 / 0 °C 3: aq. TFA / tetrahydrofuran / Ambient temperature 4: Na2CO3, Pb(OAc)4 / CH2Cl2 / 0.25 h / -78 °C 5: toluene / 3 h / 80 °C 6: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 - 0 °C 7: NaHCO3 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / Ambient temperature 8: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 9: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme

1: Na2CO3, Pb(OAc)4 / CH2Cl2 / 0.25 h / -78 °C 2: toluene / 3 h / 80 °C 3: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 - 0 °C 4: NaHCO3 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / Ambient temperature 5: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 6: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme

1: aq. TFA / tetrahydrofuran / Ambient temperature 2: Na2CO3, Pb(OAc)4 / CH2Cl2 / 0.25 h / -78 °C 3: toluene / 3 h / 80 °C 4: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 - 0 °C 5: NaHCO3 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / Ambient temperature 6: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 7: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme