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

HRID 30228

반응식

HRID 30228 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 2448772,5-Diphenyl-1H-pyrrole

시약·촉매·용매 2

HCID 962Water용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-971da28a4a5546488872b1f08a276692
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423059B2

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