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

HRID 902867노트

반응식

HRID 902867 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-96f68103cf6446ae903a6a1f93e12c11
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365205B2

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