1: 75.8 percent / triphenylphosphine, diethylamine, copper(I) iodide / palladium chloride / 18 h / Ambient temperature 2: 2.60 g / H2 / 5percent palladium-on-charcoal / ethanol / 12 h / 2585.7 Torr 3: triethylamine / diethyl ether / 4 h / 0 - 20 °C 4: 1.) NaH / 1.) THF, 0 deg C -> room temperature, 2.) room temperature, 12 h; reflux, 6 h 5: 1.) sodium methoxide / 1.) anhydrous methanol, nitrogen atmosphere, 0.5 h, 2.) anhydrous dimethylformamide, mild warming, 12 h 6: 2.33 g / 1N sodium hydroxide / 18 h / Ambient temperature View Scheme

1: 2.60 g / H2 / 5percent palladium-on-charcoal / ethanol / 12 h / 2585.7 Torr 2: triethylamine / diethyl ether / 4 h / 0 - 20 °C 3: 1.) NaH / 1.) THF, 0 deg C -> room temperature, 2.) room temperature, 12 h; reflux, 6 h 4: 1.) sodium methoxide / 1.) anhydrous methanol, nitrogen atmosphere, 0.5 h, 2.) anhydrous dimethylformamide, mild warming, 12 h 5: 2.33 g / 1N sodium hydroxide / 18 h / Ambient temperature View Scheme

1: triethylamine / diethyl ether / 4 h / 0 - 20 °C 2: 1.) NaH / 1.) THF, 0 deg C -> room temperature, 2.) room temperature, 12 h; reflux, 6 h 3: 1.) sodium methoxide / 1.) anhydrous methanol, nitrogen atmosphere, 0.5 h, 2.) anhydrous dimethylformamide, mild warming, 12 h 4: 2.33 g / 1N sodium hydroxide / 18 h / Ambient temperature View Scheme

sodium hydroxide 18 h; Ambient temperature;

1: 1.) NaH / 1.) THF, 0 deg C -> room temperature, 2.) room temperature, 12 h; reflux, 6 h 2: 1.) sodium methoxide / 1.) anhydrous methanol, nitrogen atmosphere, 0.5 h, 2.) anhydrous dimethylformamide, mild warming, 12 h 3: 2.33 g / 1N sodium hydroxide / 18 h / Ambient temperature View Scheme

1: 1.) sodium methoxide / 1.) anhydrous methanol, nitrogen atmosphere, 0.5 h, 2.) anhydrous dimethylformamide, mild warming, 12 h 2: 2.33 g / 1N sodium hydroxide / 18 h / Ambient temperature View Scheme