Indole → 4,4-di-(1H-indolyl-)butanoic acid

HRID 6946노트

반응식

HRID 6946 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH2:10]>CO>[N:1]1([CH:2]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH2:3][CH2:4][C:5]([OH:10])=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

4

반응물 2

HCID 798IndoleHCID 962Water

생성물 1

HCID 220193114,4-di-(1H-indolyl-)butanoic acid

시약·촉매·용매 1

HCID 887Methanol용매

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온도
35 °C

실험 절차

282 mg of indole (2.4 mmol) were dissolved in 10 ml of CH3OH and 5 ml of H2O; 102 mg of semisuccinic aldehyde (1 mmol) and 240 mg of dysprosium triflate-(CF3SO3)3Dy-(0.393 mmol) were added. The resulting solution was stirred at 35° C. for 24 hours. At the end of that period the methanol was removed under vacuum and the residue was extracted with ethyl acetate (3×50 ml). The organic extracts were pooled, washed with a small amount of water, dried on anhydrous Na2SO4, filtered and concentrated to dryness. The end product was isolated and purified chromatographically on an SiO2 column, using a hexane:isopropyl alcohol gradient ranging from 9:1 to 8:2.

후처리

  1. customAt the end of that period the methanol was removed under vacuum
  2. extractionthe residue was extracted with ethyl acetate (3×50 ml)
  3. washwashed with a small amount of water
  4. dry with materialdried on anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe end product was isolated
  8. custompurified chromatographically on an SiO2 column

출처 및 근거

ORD 기록
ord-ce562329315947d4a7330023ab1ce86c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084166B2

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