Indole-7-carboxaldehyde → 7-Ethenyl-1H-indole

HRID 351588

반응식

HRID 351588 반응식
[CH3:1]C(C)([O-])C.[K+].[CH:7]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[CH:7]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)=[CH2:1]

참가 물질

6

반응물 2

HCID 2734629Indole-7-carboxaldehydeHCID 23665647Potassium tert-butoxide

생성물 1

HCID 145674047-Ethenyl-1H-indole

시약·촉매·용매 3

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of methyl triphenylphosphonium bromide (5.05 g, 14.1 mmol) in tetrahydrofuran (80 mL) was added potassium tert-butoxide (1 M in tetrahydrofuran, 14.1 mL, 14.1 mmol) and the reaction stirred for 45 minutes at room temperature. Next a prepared solution of 7-formylindole (1.00 g, 6.89 mmol) in tetrahydrofuran (10 mL) was added and the reaction stirred for 1.5 hours. The reaction mixture was diluted with ethyl acetate (250 mL) and washed with an 8:1 mixture of water and 1 N hydrochloric acid (2×100 mL), saturated aqueous sodium chloride (100 mL), and dried over sodium sulfate. The solution was filtered and the filtrate concentrated under reduced pressure. The residue was subjected to silica gel chromatography. Fractions containing product were combined and concentrated under reduced pressure to provide the desired compound as a brown oil.

후처리

  1. stirringthe reaction stirred for 1.5 hours
  2. washwashed with an 8:1 mixture of water and 1 N hydrochloric acid (2×100 mL), saturated aqueous sodium chloride (100 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationThe solution was filtered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. additionFractions containing product
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-43a1ca3d2ecd4c47834d89a23cb06795
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743785B2

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