1-Phenyl-1,4-pentanedione → HCID 58310935, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-aminoacetate hydrochloride (1.378 g, 9.87 mmol) was diluted with ethanol (50 ml) then charged with TEA (8 ml, 57.4 mmol). 1-Phenylpentane-1,4-dione (1.74 g, 9.87 mmol) was then added and reaction was heated at 70° C. overnight. The reaction mixture was then diluted with 100 mL DCM and washed with water (100 mL). The aqueous was back-extracted with DCM (50 mL×2), the organics were combined, dried (Na2SO4), filtered, and concentrated to yield a crude orange oil. This oil was loaded onto a SiO2 column and purified using a 0-20% gradient of EtOAc in hexanes, affording 1.74 g (72.4% yield) of the desired ethyl 2-(2-methyl-5-phenyl-1H-pyrrol-1-yl)acetate.

Provenance & Evidence