1-(Triphenylphosphoranylidene)acetone → Methyl 3-(3-oxo-1-butenyl)indole-6-carboxylate

HRID 1108712

반응식

HRID 1108712 반응식
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1)=O.[C:16]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:18])[CH3:17]>O1CCOCC1>[O:18]=[C:16]([CH3:19])[CH:17]=[CH:1][C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1

참가 물질

4

반응물 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 735867methyl 3-formyl-1H-indole-6-carboxylate

생성물 1

HCID 53858282Methyl 3-(3-oxo-1-butenyl)indole-6-carboxylate수율 17%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of methyl 3-formylindole-6-carboxylate (368 mg) in 1,4-dioxane (10 ml) was added acetylmethylene triphenylphosphorane (1.15 g), and the mixture was stirred under reflux for 12 hours. The resulting mixture was evaporated in vacuo, redissolved with ethyl acetate and washed with 1N hydrochloric acid and brine. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of chloroform and ethyl acetate (1:2) to give methyl 3-(3-oxo-1-butenyl)indole-6-carboxylate (75 mg) as a solid.

후처리

  1. temperatureunder reflux for 12 hours
  2. customThe resulting mixture was evaporated in vacuo
  3. dissolutionredissolved with ethyl acetate
  4. washwashed with 1N hydrochloric acid and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with a mixture of chloroform and ethyl acetate (1:2)

출처 및 근거

ORD 기록
ord-86c9bf65327947cf9aca18fa86468d73
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06069156

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