Triazabicyclodecene → 1H-Pyrrole-2-carboxylic acid, 4-methyl-3-phenyl-, ethyl ester

HRID 2427405Notes

Reaction equation

HRID 2427405 reaction equation
N12CCCNC1=NCCC2.[CH3:11]/[C:12](/[N+]([O-])=O)=[CH:13]\[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:23]([O:25][C:26](=[O:30])[CH2:27][N+:28]#[C-:29])[CH3:24]>C(O)(C)C.C1COCC1>[CH2:23]([O:25][C:26]([C:27]1[NH:28][CH:29]=[C:12]([CH3:11])[C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:30])[CH3:24]

Participants

6

Reactant 3

HCID 79873TriazabicyclodeceneHCID 533707Ethyl isocyanoacetateHCID 15495201-Phenyl-2-nitropropene

Product 1

HCID 107045911H-Pyrrole-2-carboxylic acid, 4-methyl-3-phenyl-, ethyl esterYield 89.2%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1,5,7-Triazabicyclo[4.4.0]dec-5-ene on polystyrene (4.7 g, 2.6 mmol/g, 12.2 mmol) was added to a reaction mixture of trans-β-methyl-β-nitrostyrene (997 mg, 6.11 mmol) and isocyanoacetic acid ethyl ester (691 mg, 6.11 mmol) in isopropanol (5 mL) and THF (5 mL) and the reaction mixture was stirred overnight at RT under nitrogen as protective gas. The reaction mixture was filtered out and the residue washed with isopropanol and THF. The desired product 4-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.25 g, 89% of theoretical) was obtained.

Workup

  1. filtrationThe reaction mixture was filtered out
  2. washthe residue washed with isopropanol and THF

Sources & evidence

ORD record
ord-9893b2eebf384016b56aa111ff2d94d4
Source dataset
uspto-grants-2011_06
Patent number
US07968591B2

Reaction notes

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