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

HRID 30228ノート

反応式

HRID 30228 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 2448772,5-Diphenyl-1H-pyrrole

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-971da28a4a5546488872b1f08a276692
出典データセット
uspto-grants-2008_09
特許番号
US07423059B2

反応ノート

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