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Ethyl Acetate → HCID 19606368, 화합물

HRID 1603915
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HRID 1603915 반응식
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[NH:5][CH:4]=1)=[O:2].CC(C)([O-])C.[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(OCC)(=O)C>CN(C)C=O>[C:27]1([CH2:26][CH2:25][CH2:24][CH2:23][N:5]2[C:6]3[C:11](=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=3)[C:3]([CH:1]=[O:2])=[CH:4]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

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반응물 4

HCID 8857Ethyl AcetateHCID 2596681-Bromo-4-phenylbutaneHCID 19606277Methyl 3-formyl-1H-indole-5-carboxylateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 19606368HCID 19606368, 화합물수율 87%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

A solution of methyl 3-formylindole-5-carboxylate (2.234 g, 11.0 mmol) and potassium tert-butoxide (1.259 g, 11.2 mmol) in dry N,N-dimethylformamide (50 ml) was added with 1-bromo-4-phenylbutane (2.385 g, 11.2 mmol) and left under stirring at room temperature for 18 h. After that the solvent was evaporated off under reduced pressure, the resulting residue was partitioned between a NaCl saturated solution (50 ml) and chloroform (50 ml) and the aqueous phase was extracted with chloroform (3×50 ml). After drying and evaporating off the solvent under reduced pressure, a crude was obtained which was purified by chromatography through a silica gel column, eluting with n-hexane:ethyl acetate, 70:30, thereby obtaining 2.847 g of the title compound (87% yield).

후처리

  1. waitleft
  2. customAfter that the solvent was evaporated off under reduced pressure
  3. customthe resulting residue was partitioned between a NaCl saturated solution (50 ml) and chloroform (50 ml)
  4. extractionthe aqueous phase was extracted with chloroform (3×50 ml)
  5. customAfter drying
  6. customevaporating off the solvent under reduced pressure
  7. customa crude was obtained which
  8. customwas purified by chromatography through a silica gel column
  9. washeluting with n-hexane

출처 및 근거

ORD 기록
ord-85a20250ed5f4d189e8e94bbf8c48387
출처 데이터셋
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05990142

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