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 10% sodium hydroxide solution was heated to 180° C. in a Parr autoclave for 90 minutes. This process was repeated 4 more times until a total of 252.2 g of 2-carboxy-5-ethoxycarbonyl-3-(2-ethoxycarbonylethyl)-4-methylpyrrole had been treated. 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 so as to keep the temperature at <20° C. until the pH was 2. Ethyl ether (1400 mL) was added, the mixture filtered and the precipitate saved. The precipitate was extracted in a Soxhlet extractor with 500 mL of ether. The combined ether layers were washed with 250 mL water followed by 150 mL of water. The combined water layers were 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