Trifluoroacetic acid → 4-(ethoxycarbonyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid

HRID 384301Notes

Reaction equation

HRID 384301 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:19])=[C:8]([C:12]([O:14]C(C)(C)C)=[O:13])[NH:9][C:10]=1[CH3:11])=[O:5])[CH3:2].FC(F)(F)C(O)=O>O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:19])=[C:8]([C:12]([OH:14])=[O:13])[NH:9][C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 43476602-Tert-butyl 4-ethyl 3,5-dimethyl-1h-pyrrole-2,4-dicarboxylate

Product 1

HCID 2247094-(ethoxycarbonyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acidYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,5-Dimethyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 6b (5.34 g, 20 mmol) was dissolved in trifluoroacetic acid (7.4 mL, 100 mmol) and the mixture was stirred for 2 hours. The reaction was monitored by TLC until the disappearance of the starting materials. Then 40 mL of water was added. The mixture was filtered and the filter cake was washed with dichloromethane and dried to obtain the title compound 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 4-ethyl ester 6c (3.65 g, yield 86.5%) as a pink solid.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with dichloromethane
  3. customdried

Sources & evidence

ORD record
ord-d97d429ec9fd4d77bdbd557e587f6bf6
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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