Diethyl acetonedicarboxylate → Ethyl 5-benzoyl-3-ethoxycarbonyl-4-methylpyrrole-2-acetate

HRID 1282349Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 71 g. (0.37 mole) of 1-phenyl-1,2,3-butanetrione-2-oxime in 350 ml. glacial acetic acid and 50 ml. of water is added to 75.5 g. diethyl acetonedicarboxylate in 350 ml. of glacial acetic acid at 70° C. Concurrently, a mixture of 73 g. (1.12 mole) of zinc dust and 91.5 g. (1.12 mole) of anhydrous sodium acetate is added in portions at such a rate that the temperature is maintained near 100° C. After the additions are complete (about 45 minutes), the mixture is refluxed for one hour and poured into iced water. The resulting crude semisolid is collected by filtration and recrystallized twice from methanol to give ethyl 5-benzoyl-3-ethoxycarbonyl-4-methylpyrrole-2-acetate, m.p. 152-154° C. Analysis: Calcd. for C19H21NO5: C, 66.46; H, 6.16; N, 4.08%. Found: C, 66.50; H, 6.20; N, 4.17%.

Workup

customat 70° C
additionConcurrently, a mixture of 73 g
custom(about 45 minutes)
temperaturethe mixture is refluxed for one hour
filtrationThe resulting crude semisolid is collected by filtration
customrecrystallized twice from methanol

Sources & evidence

ORD record: ord-8b11fcdbd1d84700a3a2a7a476c6e964
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455703B2

Reaction notes

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