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

HRID 557163노트

반응식

HRID 557163 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

Add potassium tert-butoxide (1 M in tetrahydrofuran, 14.1 mL, 14.1 mmol) to a solution of methyl triphenylphosphonium bromide (5.05 g, 14.1 mmol) in tetrahydrofuran (80 mL) and stir the reaction mixture for 45 minutes at room temperature. Add a solution of 7-formylindole (1.00 g, 6.89 mmol) in tetrahydrofuran (10 mL) and stirred for 1.5 hours. Dilute the reaction mixture with ethyl acetate (250 mL), wash sequentially with an 8:1 mixture of water and 1 N hydrochloric acid (2×100 mL) and saturated aqueous sodium chloride (100 mL), dry over sodium sulfate, filter, and concentrate the filtrate under reduced pressure. Subject the residue silica gel chromatography. Combine fractions containing product and concentrate them under reduced pressure to provide the desired compound as a brown oil.

후처리

  1. stirringstirred for 1.5 hours
  2. washwash sequentially with an 8:1 mixture of water and 1 N hydrochloric acid (2×100 mL) and saturated aqueous sodium chloride (100 mL)
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate the filtrate under reduced pressure
  6. additionCombine fractions containing product
  7. concentrationconcentrate them under reduced pressure

출처 및 근거

ORD 기록
ord-26848bd307884ed187f181d62ab4656b
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058425B2

반응 노트

불러오는 중…