5-Methyl-2-formylpyrrole → 4-benzyloxy-5-(5-methyl-1H-pyrrol-2-yl-methylene)-1,5-dihydro-pyrrol-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-formyl-5-methylpyrrole (4 g; 36.65 mmols) and 4-benzyloxy-3-pyrrolin-2-one (8.24 g; 43.78 mmols) in DMSO (65 ml) 2N sodium hydroxyde (45 ml) was added under nitrogen atmosphere and the mixture was stirred at 60° C. for 8 hours. After dilution with water (200 ml) the yellow suspension was filtered. The crude material was taken up in ethyl acetate, stirred and filtered to give 4-benzyloxy-5-(5-methyl-1H-pyrrol-2-yl-methylene)-1,5-dihydro-pyrrol-2-one (7.7 g; 27.49 mmols) as a 4:1 Z:E mixture. Yield: 75%

Provenance & Evidence