Diethyl Carbonate → Ethyl 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate

HRID 1760733Notes

Reaction equation

HRID 1760733 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[C:10](=[O:16])[CH2:9][CH2:8]2.[C:17](=O)([O:21]CC)[O:18][CH2:19][CH3:20]>C1COCC1>[CH2:19]([O:18][C:17]([CH:9]1[CH2:8][C:7]2[C:11](=[CH:12][C:13]([O:14][CH3:15])=[C:5]([O:4][CH3:3])[CH:6]=2)[C:10]1=[O:16])=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 750185,6-Dimethoxy-1-indanone

Product 1

HCID 11514485Ethyl 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

This compound is prepared according to the procedure disclosed in EP 534859. To a suspension of sodium hydride (50% dispersion in oil, 20 g) in 240 mL of THF, diethyl carbonate was added and the mixture was stirred and refluxed for 90 min. A solution of 5,6-Dimethoxyindan-1-one (40 g) in THF (440 mL) was added, the mixture was heated under reflux for 3 h, then cooled and concentrated. Ethyl acetate (200 mL) was added, the organic layer was washed with water. The organic layer was dried over MgSO4, filtered and the ethyl acetate was removed under reduced pressure. The title product was obtained in 98% yield.

Workup

  1. customThis compound is prepared
  2. additionwas added
  3. temperaturerefluxed for 90 min
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 3 h
  6. temperaturecooled
  7. concentrationconcentrated
  8. additionEthyl acetate (200 mL) was added
  9. washthe organic layer was washed with water
  10. dry with materialThe organic layer was dried over MgSO4
  11. filtrationfiltered
  12. customthe ethyl acetate was removed under reduced pressure

Sources & evidence

ORD record
ord-befae346b6a243dfa3b89e6778b0a913
Source dataset
uspto-grants-2005_01
Patent number
US06844440B2

Reaction notes

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