1,3-Diphenyl-2-methyl-1,3-propandione → 2,5-Diphenyl-1H-pyrrole

HRID 30228Notes

Reaction equation

HRID 30228 reaction equation
[C:1]([CH:9]([C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O-])(=O)C.[NH4+:23]>O.[OH-].[Na+]>[C:17]1([C:12]2[NH:23][C:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:9][CH:11]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:19]=1

Participants

5

Reactant 2

HCID 3446371,3-Diphenyl-2-methyl-1,3-propandioneHCID 517165Ammonium Acetate

Product 1

HCID 2448772,5-Diphenyl-1H-pyrrole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

Dibenzoylethane (1.50 g, 6.30 mmol) and ammonium acetate (2.00 g, 25.2 mmol) were mixed together and the mixture was heated to 100° C. for 4 hours. The reaction mixture was cooled down to room temperature, diluted with 30 ml of water and basified with 1N NaOH until pH 14. The reaction mixture was extracted several times with chloroform. The combined organic phases were washed with 1N NaOH, water, brine and dried over MgSO4. Filtration and concentration afforded a crude product which was purified on silica gel column with hexanes/ethyl acetate (10/1) as eluant, the product was collected to yield after evaporation to dryness 0.90 g (65.2%). A light yellow solid; 1H-NMR (CDCl3): 67 ppm 7.20-7.60 (m, ArH, 10H), 6.6 (d, ArH, 2H).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionThe reaction mixture was extracted several times with chloroform
  3. washThe combined organic phases were washed with 1N NaOH, water, brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-971da28a4a5546488872b1f08a276692
Source dataset
uspto-grants-2008_09
Patent number
US07423059B2

Reaction notes

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