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

HRID 1703289노트

반응식

HRID 1703289 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f7862f327ca449be806e976b49e06bff
출처 데이터셋
uspto-grants-1982_09
특허 번호
US04351843

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