2-O-tert-butyl 4-O-ethyl 5-(3-ethoxy-3-oxoprop-1-enyl)-3-methyl-1H-pyrrole-2,4-dicarboxylate → 2-O-tert-butyl 4-O-ethyl 5-(3-ethoxy-3-oxopropyl)-3-methyl-1H-pyrrole-2,4-dicarboxylate
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:25])=[C:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[NH:9][C:10]=1[CH:11]=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:25])=[C:8]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[NH:9][C:10]=1[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:5])[CH3:2]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
5-(2-Ethoxycarbonyl-vinyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1c (24 g, 68.3 mmol) was dissolved in anhydrous ethanol (180 ml) under stirring, and added with palladium on activated carbon (2.44 g, 10%) to the solution. The resulting solution was stirred at room temperature overnight under a hydrogen atmosphere. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was filtered to remove palladium on activated carbon, and washed with a little ethanol. The filtrate was concentrated under reduced pressure to obtain the title compound 5-(2-ethoxycarbonyl-ethyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1d (23 g, yield 95%) as a white solid.
Workup
- stirringThe resulting solution was stirred at room temperature overnight under a hydrogen atmosphere
- filtrationthe reaction mixture was filtered
- customto remove palladium on activated carbon
- washwashed with a little ethanol
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-cef7c677042c483ea0c7b1dd9c7b0339
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329682B2
Reaction notes
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