Acetic Acid → HCID 12506855, compound

HRID 1368428Notes

Reaction equation

HRID 1368428 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:20])=[C:9]([C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2].C(O)(=[O:23])C.O>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH:20]=[O:23])=[C:9]([C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 683447HCID 683447, compound

Product 1

HCID 12506855HCID 12506855, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-benzoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (4.13 g, 15.2 mmol) and ceric ammonium nitrate (33 g, 4 equiv.) in 50 mL of tetrahydrofuran (THF):acetic acid (HOAc):H2O 1:1:1 was refluxed overnight. The reaction mixture was then cooled, extracted with EtOAc and then basified to pH 9 with sodium carbonate. The organic layer was then washed with brine, dried (MgSO4) and concentrated followed by column chromatography to give 3.25 g (75%) of 4-benzoyl-5-formyl-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester as a yellow solid.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionextracted with EtOAc
  3. washThe organic layer was then washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0ab447c099d4459e80e50b6acade4ce0
Source dataset
uspto-grants-2003_06
Patent number
US06573293B2

Reaction notes

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