Selenium Dioxide → Ethyl 5-(4-phenylbenzoyl)pyrrole-3-carboxylate

HRID 1980928ノート

反応式

HRID 1980928 の反応式
N1C=CC=CC=1C[N:8]1[C:12]([C:13](=[O:26])[C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[CH:11][C:10]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:9]1.O1CCOCC1.[Se](=O)=O>O>[C:20]1([C:17]2[CH:16]=[CH:15][C:14]([C:13]([C:12]3[NH:8][CH:9]=[C:10]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:11]=3)=[O:26])=[CH:19][CH:18]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 20401013Ethyl 1-(2-pyridylmethyl)-5-(4-phenylbenzoyl)pyrrole-3-carboxylate

生成物 1

HCID 12897070Ethyl 5-(4-phenylbenzoyl)pyrrole-3-carboxylate収率 75.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Ethyl 1-(2-pyridylmethyl)-5-(4-phenylbenzoyl)pyrrole-3-carboxylate (5.3 g.) was combined with 150 ml. of dioxane, 5 ml. of water and 10 g. of selenium dioxide and refluxed for approximately 16 hours. Insoluble material was separated by filtration, the filtrate was diluted with 150 ml. of ether and 150 ml. of water, the mixture equilibrated, the ether phase separated, back-washed twice with 100 ml. portions of water, filtered and concentrated to yield ethyl 5-(4-phenylbenzoyl)pyrrole-3-carboxylate (3.1 g, solid; Rf 0.4 on silica gel thin layer chromatography with ethyl acetate-1/hexane-5/5% acetic acid as eluant).

後処理

  1. customInsoluble material was separated by filtration
  2. additionthe filtrate was diluted with 150 ml
  3. customthe ether phase separated
  4. washback-washed twice with 100 ml
  5. filtrationportions of water, filtered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-9a1b8928f6ef44b7b0e2f0103d1ce50d
出典データセット
uspto-grants-1985_04
特許番号
US04511575

反応ノート

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