Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → 2-O-tert-butyl 4-O-ethyl 5-(3-ethoxy-3-oxoprop-1-enyl)-3-methyl-1H-pyrrole-2,4-dicarboxylate

HRID 2191393Notes

Reaction equation

HRID 2191393 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:20])=[C:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[NH:9][C:10]=1[CH:11]=O)=[O:5])[CH3:2].[CH2:21]([O:23][C:24]([CH:26]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:25])[CH3:22]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:20])=[C:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[NH:9][C:10]=1[CH:11]=[CH:26][C:24]([O:23][CH2:21][CH3:22])=[O:25])=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 98142842-O-tert-butyl 4-O-ethyl 5-formyl-3-methyl-1H-pyrrole-2,4-dicarboxylate

Product 1

HCID 685279692-O-tert-butyl 4-O-ethyl 5-(3-ethoxy-3-oxoprop-1-enyl)-3-methyl-1H-pyrrole-2,4-dicarboxylateYield 84%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Formyl-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1 b (23 g, 81.7 mmol) and (ethoxycarbonylmethylene)triphenylphosphorane (34.66 g, 99.4 mmol) were dissolved in 450 ml of tetrahydrofuran, and stirred at room temperature overnight under an argon atmosphere. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was concentrated under reduced pressure to obtain a yellow oil. The residue was dissolved in the solvent mixture of n-hexane and ethyl acetate (V:V=20:1), and purified by sand funnel decompression column chromatography to obtain the title compound 5-(2-ethoxycarbonyl-vinyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1c (24 g, yield 84%) as a light yellow solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto obtain a yellow oil
  3. custompurified by sand funnel decompression column chromatography

Sources & evidence

ORD record
ord-b5d3d6ec95624d939ee608e838a375e7
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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