Formation of a cyclic derivative of ethacrynic acid with diazomethane.
Samples of ethacrynic acid were treated with methanol-hydrochloric acid or with diazomethane. GLC and mass spectrometric analysis indicated that the methanol-hydrochloric acid reaction gave the expected methyl ester, whereas diazomethane treatment gave a compound containing an additional 14 mass units. Accurate mass measurement and PMR and IR spectra showed that this product was a cyclic derivative of the methyl ester of ethacrynic acid, methyl 4-(2,3-dihydro-4-ethyl-5-furyl)-2,3-dichlorophenoxyacetate. Either derivatization method can be used for development of an assay for ethacrynic acid.
D002849:Chromatography, Gas; D003500:Cyclization; D003978:Diazomethane; D004976:Ethacrynic Acid / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis; D006851:Hydrochloric Acid; D013058:Mass Spectrometry; D000432:Methanol; D008722:Methods
D003978:Diazomethane; D004976:Ethacrynic Acid; D006851:Hydrochloric Acid; D000432:Methanol