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

HRID 487695Notes

Reaction equation

HRID 487695 reaction equation
[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]

Participants

5

Reactant 2

HCID 190927132-Ethoxycarbonylbenzyltriphenylphosphonium bromideHCID 19603806HCID 19603806, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-abdb3152f250459382d19977d3282b81
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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