HCID 291759, compound → 3-(4-Methyl-1H-pyrrol-3-yl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

2-Carboxy-5-ethoxycarbonyl-3-(2-ethoxycarbonylethyl)-4-methylpyrrole (50.5 g) and 400 mL of 10% sodium hydroxide solution was heated to 180° C. in a Parr autoclave for 90 min. This process was repeated 4 more times on a total of 252.5 g of 2-carboxy-5-ethoxycarbonyl-3-(2-ethoxycarbonylethyl)-4-methylpyrrole. The five solutions were combined and rotary evaporated to a volume of about 1.8 L of thick black residue. The mixture was cooled to 10° C. in a water bath, and 50% sulfuric acid was slowly added until the pH was 2, keeping the temperature <20° C. Ethyl ether (1400 mL) was added and the mixture filtered, saving the precipitate. The precipitate was extracted in a Soxhlet apparatus with 500 mL of ether. The combined ether layers were washed with 250 mL, and then 150 mL, of water, and the water layers back extracted with 150 mL of ether. All the ether layers were rotary evaporated and the residue dried to give 123.5 g of 3-(2-carboxyethyl)-4-methylpyrrole.

Provenance & Evidence