Pyrrole → HCID 68986392, compound

HRID 2249653Notes

Reaction equation

HRID 2249653 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH:18]([CH3:20])[CH3:19])[C:10]([OH:12])=O)[CH3:2].C(Cl)(=O)C(Cl)=O.[NH:28]1[CH:32]=[CH:31][CH:30]=[CH:29]1.C[Mg]Br.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C.CN(C)C=O>[CH2:17]([O:16][C:15]1[CH:14]=[CH:13][C:9]([C:10]([C:29]2[NH:28][CH:32]=[CH:31][CH:30]=2)=[O:12])=[CH:8][C:7]=1[CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:21])[CH:18]([CH3:20])[CH3:19]

Participants

9

Reactant 5

HCID 8027Pyrrole2×HCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 17816522HCID 17816522, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68986392HCID 68986392, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8.0 g of 3-(3-ethoxy-3-oxopropyl)-4-isobutoxybenzoic acid in 80 ml of tetrahydrofuran are dropwise added 3.6 ml of oxalyl chloride and 60 μl of N,N-dimethylformamide successively, and the mixture thus obtained is stirred at ambient temperature for one hour. Then, to the reaction mixture obtained herein is dropwise added, at −70° C., a pyrrole reagent prepared from 8.5 ml of pyrrole and 82 ml of 1 mol/L solution of methylmagnesium bromide in tetrahydrofuran. After dropping, the temperature is elevated to ambient temperature over a period of one hour, and the mixture is stirred at ambient temperature for one hour. The reaction mixture is cooled with ice water, a saturated aqueous solution of ammonium chloride is dropwise added, the mixture thus obtained is stirred at ambient temperature for 15 minutes, ethyl acetate is added, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1) to obtain 5.0 g of ethyl 3-[2-isobutoxy-5-(1H-pyrrol-2-ylcarbonyl)phenyl]-propanoate as a brown-colored solid product.

Workup

  1. customthe mixture thus obtained
  2. customThen, to the reaction mixture obtained herein
  3. additionis dropwise added, at −70° C.
  4. waitthe temperature is elevated to ambient temperature over a period of one hour
  5. stirringthe mixture is stirred at ambient temperature for one hour
  6. customthe mixture thus obtained
  7. stirringis stirred at ambient temperature for 15 minutes
  8. customthe organic layer is separated
  9. customThe organic layer thus obtained
  10. washis washed with water and saturated aqueous solution of sodium chloride successively
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationthe solvent is distilled off under reduced pressure
  13. customThe residue thus obtained
  14. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-9559ae693e2c4cd2818edec9e376df90
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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