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

HRID 894634
ノート
印刷プレビュー

反応式

HRID 894634 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 12926038HCID 12926038、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone
溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-10449b1e17854b788c3c9ae21d36be12
出典データセット
uspto-grants-1981_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04284644

反応ノート

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