Ammonium Acetate → HCID 66670204, compound

HRID 1514645Notes

Reaction equation

HRID 1514645 reaction equation
[C:1]([CH:4]([CH2:15][C:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])(=O)[CH3:2].C([O-])(=O)C.[NH4+:28]>C(O)(=O)C.O>[CH3:2][C:1]1[NH:28][C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:15][C:4]=1[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 66670250HCID 66670250, compound

Product 1

HCID 66670204HCID 66670204, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 6.00 g portion of benzyl 2-acetyl-4-oxo-4-phenylbutanoate was dissolved in a mixture of 54 ml acetic acid and 5.4 ml water, and 14.9 g of ammonium acetate was added, followed by stirring at 100° C. for 1 hour. After evaporation of the solvent under a reduced pressure and subsequent addition of ethyl acetate-water, the ethyl acetate layer was washed with a 1 M sodium hydroxide aqueous solution and saturated brine, followed by drying with anhydrous sodium sulfate. Then, the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5-1:4) to obtain 3.84 g of benzyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate as a light purple solid.

Workup

  1. additionwas added
  2. customAfter evaporation of the solvent
  3. additionunder a reduced pressure and subsequent addition of ethyl acetate-water
  4. washthe ethyl acetate layer was washed with a 1 M sodium hydroxide aqueous solution and saturated brine
  5. dry with materialby drying with anhydrous sodium sulfate
  6. customThen, the solvent was evaporated under a reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5-1:4)

Sources & evidence

ORD record
ord-3490bfad5af64fe0ba92395bf0f7b1e0
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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