Benzyl Chloride → Ethyl 1-benzyl-5-chloroindole-2-carboxylate

HRID 902867ノート

反応式

HRID 902867 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH2:22]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 78518Ethyl 5-chloroindole-2-carboxylate

生成物 1

HCID 13295699Ethyl 1-benzyl-5-chloroindole-2-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Ethyl 5-chloroindole-2-carboxylate (1.4 g) was dissolved in N,N-dimethylformamide (30 ml), and potassium carbonate (2.9 g) and benzyl chloride (2.4 ml) were added. The mixture was heated and stirred for 1.5 hours on a hot bath controlled to 100° C. The reaction mixture was concentrated under reduced pressure, and the residue was poured into ice water and extracted with ethyl acetate. The resultant organic layer was washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by column chromatagraphy on silica gel (ethyl acetate:hexane=1:19) and crystallized from diethyl ether-hexane to obtain the title compound (1.6 g).

後処理

  1. temperatureThe mixture was heated
  2. customcontrolled to 100° C
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was poured into ice water
  5. extractionextracted with ethyl acetate
  6. washThe resultant organic layer was washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was purified by column chromatagraphy on silica gel (ethyl acetate:hexane=1:19)
  10. customcrystallized from diethyl ether-hexane

出典と根拠

ORDレコード
ord-96f68103cf6446ae903a6a1f93e12c11
出典データセット
uspto-grants-2008_04
特許番号
US07365205B2

反応ノート

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