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

HRID 1108712

反応式

HRID 1108712 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-86c9bf65327947cf9aca18fa86468d73
出典データセット
uspto-grants-2000_05
特許番号
US06069156

関連ノート

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