Dimethyl Carbonate → 3-NAPHTHALEN-1-YL-3-OXO-PROPIONIC ACID METHYL ESTER

HRID 1059116Notes

Reaction equation

HRID 1059116 reaction equation
[CH3:1][C:2]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)=[O:3].[H-].[Na+].[CH3:16][O:17][C:18](=O)[O:19]C>CCCCCC.C(OCC)(=O)C>[C:4]1([C:2](=[O:3])[CH2:1][C:18]([O:17][CH3:16])=[O:19])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 136631-AcetylnaphthaleneHCID 24758Sodium hydride

Product 1

HCID 27601593-NAPHTHALEN-1-YL-3-OXO-PROPIONIC ACID METHYL ESTERYield 73%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

10.2 g(59.9 mmol) of 1-acetonaphthone and 4.8 g(60% in mineral oil, 120 mmol) of sodium hydride were added to 100 ml of dimethylcarbonate and the mixture was refluxed for 24 hours. The solvent was removed under reduced pressure, 100 mg of 1N aqueous HCl solution was added to the residue, and the resulting mixture was extracted with 100 ml of ethyl acetate. The organic layer was washed with water(100 ml×3), dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography(eluent: n-hexane/ethyl acetate=90/10, v/v) to give 10.0 g (43.8 mmol, Yield 73%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. customThe solvent was removed under reduced pressure, 100 mg of 1N aqueous HCl solution
  3. additionwas added to the residue
  4. extractionthe resulting mixture was extracted with 100 ml of ethyl acetate
  5. washThe organic layer was washed with water(100 ml×3)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-623d336008594679bb65f6452b6b5820
Source dataset
uspto-grants-2003_02
Patent number
US06518429B2

Reaction notes

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