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

HRID 894634Notes

Reaction equation

HRID 894634 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-10449b1e17854b788c3c9ae21d36be12
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

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