sodium hydroxide in methanol; water T=30°C; 1.5 h;

1.1: 88 percent / NaH / dimethylformamide; various solvent(s) / 0 - 20 °C 2.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -78 °C 2.2: 85 percent / tetrahydrofuran; hexane / -78 - 20 °C 3.1: ozone / -78 °C 3.2: 80 percent / pyridine / CH2Cl2 / -78 - 20 °C 4.1: H2 / 10 percent Pt/C / methanol / 72 h / 2585.74 Torr 4.2: 70 percent / H2 / 10 percent Pd/C / methanol / 96 h / 2585.74 Torr 5.1: 96 percent / NaOH / methanol; H2O / 1.5 h / 30 °C View Scheme

1.1: ozone / -78 °C 1.2: 80 percent / pyridine / CH2Cl2 / -78 - 20 °C 2.1: H2 / 10 percent Pt/C / methanol / 72 h / 2585.74 Torr 2.2: 70 percent / H2 / 10 percent Pd/C / methanol / 96 h / 2585.74 Torr 3.1: 96 percent / NaOH / methanol; H2O / 1.5 h / 30 °C View Scheme

1.1: H2 / 10 percent Pt/C / methanol / 72 h / 2585.74 Torr 1.2: 70 percent / H2 / 10 percent Pd/C / methanol / 96 h / 2585.74 Torr 2.1: 96 percent / NaOH / methanol; H2O / 1.5 h / 30 °C View Scheme