Dimethylformamide → HCID 58629126, compound

HRID 1678059Notes

Reaction equation

HRID 1678059 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[NH:7]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8]1.CN(C=O)C.IC(C)C>CCOCC.O>[CH:2]([N:7]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8]1)([CH3:3])[CH3:1]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 27377933-AcetylpyrroleHCID 23665647Potassium tert-butoxide

Product 1

HCID 58629126HCID 58629126, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Potassium t-butoxide (6.7 g, 60 mmol) was added to a stirred 0° C. solution of 1-(1H-pyrrol-3-yl)ethanone (5.0 g, 46 mmol) of DMF (150 mL). After stirring for 30 minutes, 2-iodopropane (10.1 g, 60 mmol) was added and the mixture was stirred overnight at approximately 25° C. The mixture was diluted with Et2O and H2O. The portions were separated, and the aqueous portion was extracted two more times. The organic portions were combined and washed with brine and then dried with Na2SO4. The mixture was filtered and the solvent removed in vacuo. The crude product was purified by flash chromatography (30 percent ether/pentane over silica gel), affording 3.9 g of yellow oil.

Workup

  1. stirringthe mixture was stirred overnight at approximately 25° C
  2. customThe portions were separated
  3. extractionthe aqueous portion was extracted two more times
  4. washwashed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationThe mixture was filtered
  7. customthe solvent removed in vacuo
  8. customThe crude product was purified by flash chromatography (30 percent ether/pentane over silica gel)

Sources & evidence

ORD record
ord-43705e5815e04005ab7b400c2e27adf4
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

Loading…