sodium hydroxide in tetrahydrofuran; methanol T=25°C; 20 h;

1: 99 percent / H2 / Pd/C / ethanol / 25 °C 2: 82 percent / aq. NaOH / tetrahydrofuran; methanol / 20 h / 25 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.58 h / -78 °C 1.2: 67 percent / tetrahydrofuran; hexane / -78 - 20 °C 2.1: 99 percent / H2 / Pd/C / ethanol / 25 °C 3.1: 82 percent / aq. NaOH / tetrahydrofuran; methanol / 20 h / 25 °C View Scheme

lithium hydroxide monohydrate; water in tetrahydrofuran; methanol 6 h; Inert atmosphere;