Ethyl 2-acetyl-4-oxo-4-phenylbutanoate → Ethyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate

HRID 554169Notes

Reaction equation

[C:1]([CH:4]([CH2:10][C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)[CH3:2].C([O-])(=O)C.[NH4+:23]>C(O)(=O)C>[CH3:2][C:1]1[NH:23][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 2-acetyl-4-oxo-4-phenylbutanoate (3.0 g) and ammonium acetate (1.39 g) were added to acetic acid (20 mL), and the mixture was stirred at 80° C. for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→1:1) to give the title compound as a brown solid (yield 1.25 g, 45%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→1:1)

Sources & evidence

ORD record: ord-b8aa0cb2025d4c5e913d727aaca88dc1
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

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