1-Phenyl-1,4-pentanedione → HCID 58310935, compound

HRID 1189574Notes

Reaction equation

HRID 1189574 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:9]1([C:15](=O)[CH2:16][CH2:17][C:18](=O)[CH3:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(O)C.C(Cl)Cl>[CH3:19][C:18]1[N:2]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 1363711-Phenyl-1,4-pentanedioneHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 58310935HCID 58310935, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 2-aminoacetate hydrochloride (1.378 g, 9.87 mmol) was diluted with ethanol (50 ml) then charged with TEA (8 ml, 57.4 mmol). 1-Phenylpentane-1,4-dione (1.74 g, 9.87 mmol) was then added and reaction was heated at 70° C. overnight. The reaction mixture was then diluted with 100 mL DCM and washed with water (100 mL). The aqueous was back-extracted with DCM (50 mL×2), the organics were combined, dried (Na2SO4), filtered, and concentrated to yield a crude orange oil. This oil was loaded onto a SiO2 column and purified using a 0-20% gradient of EtOAc in hexanes, affording 1.74 g (72.4% yield) of the desired ethyl 2-(2-methyl-5-phenyl-1H-pyrrol-1-yl)acetate.

Workup

  1. customreaction
  2. washwashed with water (100 mL)
  3. extractionThe aqueous was back-extracted with DCM (50 mL×2)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a crude orange oil
  8. custompurified

Sources & evidence

ORD record
ord-82355a0b03e64c789acbaa7eb35018aa
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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