Benzenesulfonyl chloride → 1-(benzenesulfonyl)-1H-indole-5-carbaldehyde

HRID 84180

反応式

HRID 84180 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12]C)=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:16]1([S:22]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([CH:10]=[O:12])=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 2737635methyl 1H-indole-5-carboxylate

生成物 1

HCID 177503871-(benzenesulfonyl)-1H-indole-5-carbaldehyde収率 91.1%

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 6344Dichloromethane溶媒

実験手順

After a suspension of methyl indole-5-carboxylate (4) (1.00 g, 6.89 mmol), tetrabutylammonium bisulfate (0.35 g, 1.03 mmol) and KOH (0.77 g, 13.78 mmol) in CH2Cl2 (30 mL) was stirred for 20 min, benzenesulfonyl chloride (1.32 ml, 10.33 mmol) was added. The reaction mixture was stirred at room temperature overnight before it was quenched with water and extracted with CH2Cl2 (20 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to give a yellow residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1:2) to afford 5 (1.79 g) as a white solid. 1H NMR (500 MHz, CDCl3): δ6.78 (d, J=3.6 Hz, 1H), 7.45-7.48 (m, 2H), 7.55-7.58 (m, 1H), 7.67 (d, J=3.7 Hz, 1H), 7.85-7.87 (m, 1H), 7.89 (d, J=7.6 Hz, 2H), 8.06 (s, 1H), 8.11 (d, J=8.6 Hz, 1H), 10.03 (s, 1H).

後処理

  1. stirringThe reaction mixture was stirred at room temperature overnight before it
  2. customwas quenched with water
  3. extractionextracted with CH2Cl2 (20 mL×3)
  4. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow residue, which
  7. customwas purified by silica gel chromatography (EtOAc:n-hexane=1:2)

出典と根拠

ORDレコード
ord-86d35d51ee7341c0be11b7592136687c
出典データセット
uspto-grants-2014_09
特許番号
US08846748B2

関連ノート

読み込み中…