1-Indanone → Methyl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate

HRID 2304010

Reaction equation

HRID 2304010 reaction equation
[H-].[Na+].[C:3](=[O:7])([O-])[O:4][CH3:5].[C:8]1(=[O:17])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1>C1C=CC=CC=1>[O:17]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH:9]1[C:3]([O:4][CH3:5])=[O:7]

Participants

5

Reactant 3

HCID 67351-IndanoneHCID 24758Sodium hydrideHCID 4585885Methylcarbonate

Product 1

HCID 312866Methyl 1-oxo-2,3-dihydro-1H-indene-2-carboxylateYield 17.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The reaction is carried out according to J. Med. Chem., 1970, 650. A suspension of 6.75 g of sodium hydride at 80% in oil and 45 g of methyl carbonate in 120 ml of benzene are mixed together. 11.9 g of 1-indanone dissolved in 100 ml of benzene are added, at 60° C., over 1 and a half hours and the mixture is then refluxed. After 1 hour, the benzene is distilled off. Xylene is added and the mixture is again refluxed. After 1 hour, it is cooled, 30 ml of AcOH are added and the resulting mixture is poured onto 200 ml of a water/ ice mixture containing 30 ml of 1N HCl. The insoluble material is removed by filtration and the filtrate is extracted with Et2O. The extracts are washed with water, with saturated NaHCO3 solution, with water, with saturated NaCl solution and then dried over Na2SO4. The product is chromatographed on silica, eluting with EtOAc/hexane (1.3; v/v) in order to obtain 3.05 g of the expected compound.

Workup

  1. additionare mixed together
  2. additionare added, at 60° C., over 1 and a half hours
  3. temperaturethe mixture is then refluxed
  4. distillationthe benzene is distilled off
  5. additionXylene is added
  6. temperaturethe mixture is again refluxed
  7. waitAfter 1 hour
  8. temperatureit is cooled
  9. addition30 ml of AcOH are added
  10. additionthe resulting mixture is poured onto 200 ml of a water/ ice mixture
  11. additioncontaining 30 ml of 1N HCl
  12. customThe insoluble material is removed by filtration
  13. extractionthe filtrate is extracted with Et2O
  14. washThe extracts are washed with water, with saturated NaHCO3 solution, with water, with saturated NaCl solution
  15. dry with materialdried over Na2SO4
  16. customThe product is chromatographed on silica
  17. washeluting with EtOAc/hexane (1.3; v/v) in order

Sources & evidence

ORD record
ord-97596392208f41a28ffaf1d4fb2f0ef5
Source dataset
uspto-grants-2002_08
Patent number
US06433185B1

Linked notes

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