n-butyllithium

1: 95 percent / LiBr / acetone / 6 h / Heating 2: 91 percent / H2; Et3N / Pd/C / ethanol; methanol / 24 h / 20 °C 3: 90 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1: 95 percent / PTSA / toluene / 4 h / Heating 2: 86 percent / LDA / tetrahydrofuran / -78 - 20 °C 3: 100 percent / PTSA / methanol / 4 h / Heating 4: 85 percent / Et3N / CH2Cl2 / 4 h / 20 °C 5: 95 percent / LiBr / acetone / 6 h / Heating 6: 91 percent / H2; Et3N / Pd/C / ethanol; methanol / 24 h / 20 °C 7: 90 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1: H2SO4 / toluene / 6 h / Heating 2: 31.2 g / NaBH4 / ethanol / 1.5 h / 0 - 20 °C 3: 95 percent / PTSA / toluene / 4 h / Heating 4: 86 percent / LDA / tetrahydrofuran / -78 - 20 °C 5: 100 percent / PTSA / methanol / 4 h / Heating 6: 85 percent / Et3N / CH2Cl2 / 4 h / 20 °C 7: 95 percent / LiBr / acetone / 6 h / Heating 8: 91 percent / H2; Et3N / Pd/C / ethanol; methanol / 24 h / 20 °C 9: 90 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1: 31.2 g / NaBH4 / ethanol / 1.5 h / 0 - 20 °C 2: 95 percent / PTSA / toluene / 4 h / Heating 3: 86 percent / LDA / tetrahydrofuran / -78 - 20 °C 4: 100 percent / PTSA / methanol / 4 h / Heating 5: 85 percent / Et3N / CH2Cl2 / 4 h / 20 °C 6: 95 percent / LiBr / acetone / 6 h / Heating 7: 91 percent / H2; Et3N / Pd/C / ethanol; methanol / 24 h / 20 °C 8: 90 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1: 91 percent / H2; Et3N / Pd/C / ethanol; methanol / 24 h / 20 °C 2: 90 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1: 1.) Bu2BOTf, i-Pr2NEt, 3.) H2O2 / 1.) CH2Cl2, 0 deg C, 2.) CH2Cl2, -78 deg C, 1h, then 0 deg C, 1.5 h, 3.) CH2Cl2, methanol, pH 7 phosphate buffer, 0 deg C, 1 h 2: 1.) LDA, 2.) LiAlH4 / 1.) THF, 0 deg C, 2.) THF, 0 deg C View Scheme