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

HRID 557163ノート

反応式

HRID 557163 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

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.

後処理

  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

出典と根拠

ORDレコード
ord-26848bd307884ed187f181d62ab4656b
出典データセット
uspto-grants-2011_11
特許番号
US08058425B2

反応ノート

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