1.1: hydrogen; potassium hydroxide; 5 palladium on charcoal / methanol / 2 h 2.1: sodium hydride / ethylene glycol dimethyl ether; mineral oil / 3.75 h / -40 - 20 °C / |Inert atmosphere; |Reflux 3.1: acetic acid / tetrahydrofuran; water / 20 °C 4.1: hydrogen; potassium hydroxide; 5 palladium on charcoal / methanol / 20 °C 5.1: potassium carbonate; tetrabutylammomium bromide / acetone / 30 °C 6.1: water; potassium hydroxide / methanol / 3 h / |Reflux 6.2: pH 2 View Scheme