Piperidine → Ethyl 5-[(E)-2-ethoxycarbonylvinyl]-3-methyl-1H-pyrrole-2-carboxylate

HRID 72773

Reaction equation

[CH:1]([C:3]1[NH:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:13])[CH:4]=1)=O.[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15]C([O-])=O.N1CCCCC1>N1C=CC=CC=1>[CH2:21]([O:20][C:14](/[CH:15]=[CH:1]/[C:3]1[NH:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:13])[CH:4]=1)=[O:19])[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 5-formyl-3-methyl-1H-pyrrole-2-carboxyate 470 mg, monoethyl malonate 378 mg, piperidine 0.05 mL and pyridine 6 mL were mixed and stirred at 100° C. for 38 hours. Ice water was added to the reaction liquid and the precipitate was recovered by filtration. The precipitate was washed with water and dried in flowing air under heating to provide 311 mg of the title compound.

Workup

filtrationthe precipitate was recovered by filtration
washThe precipitate was washed with water
customdried
temperatureunder heating

Sources & evidence

ORD record: ord-fb2dddac9b4b492ab2f73cd7baa61606
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829000B2

Linked notes

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