Diethyl Malonate → Diethyl {[(5-benzoyl-1H-pyrrol-2-yl)acetyl]oxy}propanedioate

HRID 1090814Notes

Reaction equation

[C:1]([C:9]1[NH:10][CH:11]=[CH:12][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[C:25]([O-:28])(=[O:27])[CH3:26].[Na+]>C(O)(=O)C.C(OCC)C.O.O.C([O-])(=O)C.[Mn+3].C([O-])(=O)C.C([O-])(=O)C>[C:1]([C:9]1[NH:10][C:11]([CH2:26][C:25]([O:28][CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:14]([O:22][CH2:23][CH3:24])=[O:21])=[O:27])=[CH:12][CH:13]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-benzoylpyrrole (855 mg, 5 mmol), diethyl malonate (800 mg, 5 mmol), manganese(III) acetate dihydrate (4560 mg, 15 mmol) and sodium acetate (820 mg, 10 mmol) in acetic acid (30 mL) was stirred at 70° C. under a nitrogen atmosphere. The reaction mixture was diluted with diethyl ether and filtered. The filtrate was washed with 10% aqueous sodium hydroxide and saturated aqueous sodium chloride, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by column chromatography on silica eluting with hexane/ethyl acetate (70:30) to provide 1.00 g (57%) of diethyl (5-benzoylpyrrol-2-yl)acetoxy-methanedicarboxylate.

Workup

filtrationfiltered
washThe filtrate was washed with 10% aqueous sodium hydroxide and saturated aqueous sodium chloride
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica eluting with hexane/ethyl acetate (70:30)

Sources & evidence

ORD record: ord-5c72ba68032442c5a009dccd10bf06b8
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05082950

Reaction notes

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