P-Anisidine → 1-(4-Methoxy-phenyl)-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 642484Notes

Reaction equation

HRID 642484 reaction equation
Br[CH2:2][CH:3]=O.C(OC(OCC)CBr)C.O.O.C(O)(=O)C(O)=O.[Na].[C:23]([O:29][CH2:30][CH3:31])(=[O:28])[CH2:24][C:25]([CH3:27])=O.[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=1>C(O)C>[CH2:30]([O:29][C:23]([C:24]1[CH:3]=[CH:2][N:40]([C:37]2[CH:38]=[CH:39][C:34]([O:33][CH3:32])=[CH:35][CH:36]=2)[C:25]=1[CH3:27])=[O:28])[CH3:31]

Participants

7

Reactant 5

HCID 7732P-AnisidineHCID 61373Oxalic acid dihydrateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 105131Acetaldehyde, bromo-HCID 87089461Ethyl acetoacetatesodium salt

Product 1

HCID 684287141-(4-Methoxy-phenyl)-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Bromoacetaldehyde (prepared from the distillates from heating 18.212 g of 2-bromoacetaldehyde diethyl acetal and 25.63 g of oxalic acid dihydrate, see U.S. Pat. No. 4,087,539 for detail) was added to an ice/water bath cooled mixture of ethyl acetoacetate sodium salt (9.84 g) in ethanol (100 mL) carefully; after addition, the mixture was stirred at rt for 1 h and para-anisidine (9.56 g) was added, the resulting mixture was subsequently refluxed in an oil bath for 1 h. Then, reaction was cooled, solvents were removed, the residue was partitioned between EtOAc and 1 M HCl aqueous solution; the organic phase was sequentially washed with water, sat. NaCl solution and dried over anhydrous sodium sulfate, filtered, concentrated; the resulting residue was column-purified to give the desired product (8.08 g). The title compound, ESI MS (m/z): 260 (M+H)+.

Workup

  1. addition4,087,539 for detail) was added to an ice/water bath
  2. temperaturecooled
  3. additionafter addition
  4. temperaturethe resulting mixture was subsequently refluxed in an oil bath for 1 h
  5. customThen, reaction
  6. temperaturewas cooled
  7. customsolvents were removed
  8. customthe residue was partitioned between EtOAc and 1 M HCl aqueous solution
  9. washthe organic phase was sequentially washed with water, sat. NaCl solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customthe resulting residue was column-purified

Sources & evidence

ORD record
ord-d0286613caf64079ad6b5a02f4a119a1
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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