sodium hydroxide in ethanol Hydrolysis; 20 h; Heating;

1.1: n-BuLi; iPr2NH / tetrahydrofuran / 1 h / -78 °C 1.2: tetrahydrofuran / -78 - 20 °C 1.3: 6N HCl / CH2Cl2 / 1 h / Heating 2.1: 100 percent / thionyl chloride / 1 h / Heating 3.1: n-Buli; iPr2NH / tetrahydrofuran / 0.5 h / 0 °C 3.2: tetrahydrofuran / -78 - 20 °C 4.1: TBAF / tetrahydrofuran; methanol / Heating View Scheme

1: PDC; PTFA / CH2Cl2 / 20 °C 2: TBAF / tetrahydrofuran; methanol / Heating View Scheme

1.1: 100 percent / thionyl chloride / 1 h / Heating 2.1: n-Buli; iPr2NH / tetrahydrofuran / 0.5 h / 0 °C 2.2: tetrahydrofuran / -78 - 20 °C 3.1: TBAF / tetrahydrofuran; methanol / Heating View Scheme

1.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 1.2: 84 percent / tetrahydrofuran; hexane / -78 - 20 °C 2.1: 75 percent / pyridinium dichromate / dimethylformamide / 20 h / 20 °C 3.1: 93 percent / NaOH / ethanol / 20 h / Heating View Scheme

1: sodium hydroxide / ethanol / 12 h / 20 °C 2: hydrogen; palladium 10 on activated carbon / ethanol / 20 °C 3: iodine; potassium carbonate / methanol / 4 h / 60 °C View Scheme

diethyl ether; benzene