Phenylacetyl chloride → 1-(5-Nitro-indol-1-yl)-2-phenyl-ethanone

HRID 1517938ノート

反応式

HRID 1517938 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[H-].[Na+].[C:15]1([CH2:21][C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:22](=[O:23])[CH2:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:8]=[CH:7]2)([O-:3])=[O:2]

参加物

7

反応物 4

HCID 7679Phenylacetyl chlorideHCID 225235-NitroindoleHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

生成物 1

HCID 593348921-(5-Nitro-indol-1-yl)-2-phenyl-ethanone

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

300 mg 5-nitroindole are dissolved in 10 ml of tetrahydrofuran. 81 mg sodium hydride (60% in mineral oil) are added and the mixture is stirred for 1 hour at ambient temperature. Then 294 μl phenylacetic acid chloride are added dropwise and the mixture is stirred for another 3 hours. It is divided between saturated ammonium chloride solution and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried on magnesium sulphate. The solvents are eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 10:1 to 1:3).

後処理

  1. stirringthe mixture is stirred for another 3 hours
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. customthe combined organic phases are dried on magnesium sulphate
  4. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 10:1 to 1:3)

出典と根拠

ORDレコード
ord-b65deb02a7914a9597000053f2ca916a
出典データセット
uspto-grants-2012_07
特許番号
US08232312B2

反応ノート

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