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

HRID 351588ノート

反応式

HRID 351588 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

HCID 145674047-Ethenyl-1H-indole

試薬・触媒・溶媒 3

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-43a1ca3d2ecd4c47834d89a23cb06795
出典データセット
uspto-grants-2004_06
特許番号
US06743785B2

反応ノート

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