Sodium Hydroxide → 4-phenyl-1H-pyrrole-2-carboxylic acid

Participants

Reaction Steps

A mixture of ethyl 4-phenyl-1H-pyrrole-2-carboxylate (700 mg, 3.25 mmol), aqueous sodium hydroxide (10% w/v, 10 mL) and ethanol (10 mL) were stirred at room temperature over night. The ethanol was evaporated in vacuo, then water (20 mL) was added and the organics were extracted with ethyl acetate (3×20 mL). The aqueous layer was acidified with 2N HCl (to pH 3) and extracted with ethyl acetate (3×20 mL). The combined organic layer was washed with water, brine (20 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 4-phenyl-1H-pyrrole-2-carboxylic acid (400 mg, 66%) as a solid.

Provenance & Evidence