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Dimethylformamide → 5-methoxycarbonylspiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one

HRID 894634
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HRID 894634 반응식
[C:1]([C:4]1[CH:15]=[CH:14][C:7]2[O:8][C:9]3([C:12](=[O:13])[C:6]=2[CH:5]=1)[CH2:11][CH2:10]3)([OH:3])=[O:2].[C:16](=O)([O-])O.[Na+].CN(C)C=O.S(OC)(OC)(=O)=O>CC(C)=O>[CH3:16][O:2][C:1]([C:4]1[CH:15]=[CH:14][C:7]2[O:8][C:9]3([C:12](=[O:13])[C:6]=2[CH:5]=1)[CH2:11][CH2:10]3)=[O:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 12926038HCID 12926038, 화합물

생성물 1

HCID 129260395-methoxycarbonylspiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one수율 58.5%

시약·촉매·용매 1

HCID 180Acetone
용매

실험 절차

5-Carboxyspiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (2 g.) and sodium hydrogen carbonate (1.25 g.) were suspended in acetone (50 ml.) and N,N-dimethylformamide (5 ml.) and, under stirring, dimethyl sulfate (2 ml.) was added dropwise to the mixture. The reaction mixture was refluxed under heating for 24 hours, and, after cooling, the solvent was evaporated off under reduced pressure. The residue was diluted with water and the solution was extracted with ethyl acetate. The extract was washed with aqueous solution of sodium hydrogen carbonate and dried. After removing the solvent by evaporation under reduced pressure, the residue was recrystallized from methanol to give colorless needles of 5-methoxycarbonylspiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (1.25 g.).

후처리

  1. temperatureThe reaction mixture was refluxed
  2. temperatureunder heating for 24 hours
  3. temperatureafter cooling
  4. customthe solvent was evaporated off under reduced pressure
  5. additionThe residue was diluted with water
  6. extractionthe solution was extracted with ethyl acetate
  7. washThe extract was washed with aqueous solution of sodium hydrogen carbonate
  8. customdried
  9. customAfter removing the solvent
  10. customby evaporation under reduced pressure
  11. customthe residue was recrystallized from methanol

출처 및 근거

ORD 기록
ord-10449b1e17854b788c3c9ae21d36be12
출처 데이터셋
uspto-grants-1981_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04284644

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