Water → 1-(2-chloro-4-(1-pentyloxy)benzyl)-4-ethenyl-2-methyl-1H-imidazole-5-carbaldehyde

HRID 1828818노트

반응식

HRID 1828818 반응식
[Cl-].[Li+].Br[C:4]1[N:5]=[C:6]([CH3:25])[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:14][C:13]=2[Cl:24])[C:8]=1[CH:9]=[O:10].[CH:26]([Sn](CCCC)(CCCC)CCCC)=[CH2:27].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:24][C:13]1[CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:16]=[CH:17][C:12]=1[CH2:11][N:7]1[C:8]([CH:9]=[O:10])=[C:4]([CH:26]=[CH2:27])[N:5]=[C:6]1[CH3:25]

참가 물질

7

반응물 4

HCID 962WaterHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 22058585HCID 22058585, 화합물

생성물 1

HCID 220586901-(2-chloro-4-(1-pentyloxy)benzyl)-4-ethenyl-2-methyl-1H-imidazole-5-carbaldehyde수율 87.7%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

Lithium chloride (180 mg) was suspended in 1,4-dioxane (10 ml), and 4-bromo-1-(2-chloro-4-(1-pentyloxy)benzyl)-2-methyl-1H-imidazole-5-carbaldehyde (707 mg), vinyltributyltin (617 mg) and tetrakis(triphenylphosphine)palladium(0) (102 mg) were added. The mixture was refluxed under heating for 12 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was applied to silica gel column chromatography and eluted with hexane/ethyl acetate=5/1. The objective fraction was concentrated under reduced pressure to give 1-(2-chloro-4-(1-pentyloxy)benzyl)-4-ethenyl-2-methyl-1H-imidazole-5-carbaldehyde(538 mg) as a pale-yellow gum.

후처리

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 12 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with hexane/ethyl acetate=5/1
  8. concentrationThe objective fraction was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-787b8e38b06149adb4010be6281ff055
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07060721B1

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