2-Ethoxycarbonylbenzyltriphenylphosphonium bromide → 4-Tert-butyl-2-[5-{2-(2-ethoxycarbonylphenyl)ethenyl}benzofuran-2-yl]thiazole

HRID 487695노트

반응식

HRID 487695 반응식
[Br-].[CH2:2]([O:4][C:5]([C:7]1[CH:32]=[CH:31][CH:30]=[CH:29][C:8]=1[CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:6])[CH3:3].[C:33]([C:37]1[N:38]=[C:39]([C:42]2[O:43][C:44]3[CH:50]=[CH:49][C:48]([CH:51]=O)=[CH:47][C:45]=3[CH:46]=2)[S:40][CH:41]=1)([CH3:36])([CH3:35])[CH3:34]>C(#N)C.N12CCCN=C1CCCCC2>[C:33]([C:37]1[N:38]=[C:39]([C:42]2[O:43][C:44]3[CH:50]=[CH:49][C:48]([CH:51]=[CH:9][C:8]4[CH:29]=[CH:30][CH:31]=[CH:32][C:7]=4[C:5]([O:4][CH2:2][CH3:3])=[O:6])=[CH:47][C:45]=3[CH:46]=2)[S:40][CH:41]=1)([CH3:36])([CH3:35])[CH3:34]

참가 물질

5

반응물 2

HCID 190927132-Ethoxycarbonylbenzyltriphenylphosphonium bromideHCID 196038064-Tert-butyl-2-(5-formylbenzofuran-2-yl)thiazole

생성물 1

HCID 539832274-Tert-butyl-2-[5-{2-(2-ethoxycarbonylphenyl)ethenyl}benzofuran-2-yl]thiazole수율 65%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene용매

실험 절차

To a solution of 2-ethoxycarbonylbenzyltriphenylphosphonium bromide (605 mg) and 4-tert-butyl-2-(5-formylbenzofuran-2-yl)thiazole (285 mg) in acetonitrile (5.00 ml), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.317 ml) was added. The resulting solution was heated under reflux for 10 hours. After concentration under reduced pressure, diisopropyl ether was added to the residue. The resulting insoluble material was removed by filtration. After concentration of filtrate under reduced pressure, n-heptane was added to the residue. The resulting insoluble material removed again by filtration. After concentration of filtrate, the residue was subjected to column chromatography on silica gel and eluted with a mixture of n-hexane and ethyl acetate. The fractions containing object compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-[5-{2-(2-ethoxycarbonylphenyl)ethenyl}benzofuran-2-yl]thiazole (280 mg) as a mixture of E and Z isomer as a viscous oil, which was used in the next step without further purification.

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 10 hours
  3. concentrationAfter concentration under reduced pressure, diisopropyl ether
  4. additionwas added to the residue
  5. customThe resulting insoluble material was removed by filtration
  6. additionAfter concentration of filtrate under reduced pressure, n-heptane was added to the residue
  7. customThe resulting insoluble material removed again by filtration
  8. washeluted with a mixture of n-hexane and ethyl acetate
  9. additionThe fractions containing object compound
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-abdb3152f250459382d19977d3282b81
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05296495

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