2-O-tert-butyl 4-O-ethyl 5-(3-ethoxy-3-oxoprop-1-enyl)-3-methyl-1H-pyrrole-2,4-dicarboxylate → 2-O-tert-butyl 4-O-ethyl 5-(3-ethoxy-3-oxopropyl)-3-methyl-1H-pyrrole-2,4-dicarboxylate

Participants

Reaction Steps

5-(2-Ethoxycarbonyl-vinyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1c (24 g, 68.3 mmol) was dissolved in anhydrous ethanol (180 ml) under stirring, and added with palladium on activated carbon (2.44 g, 10%) to the solution. The resulting solution was stirred at room temperature overnight under a hydrogen atmosphere. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was filtered to remove palladium on activated carbon, and washed with a little ethanol. The filtrate was concentrated under reduced pressure to obtain the title compound 5-(2-ethoxycarbonyl-ethyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1d (23 g, yield 95%) as a white solid.

Provenance & Evidence