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

HRID 487695ノート

反応式

HRID 487695 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-abdb3152f250459382d19977d3282b81
出典データセット
uspto-grants-1994_03
特許番号
US05296495

反応ノート

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