Toluene → 2,3-Dihydro-5-methoxy-2,2-dimethyl-1H-inden-1-one

HRID 494935Notes

Reaction equation

HRID 494935 reaction equation
C[C:2](C)([O-:4])C.[K+].COC1C=[C:11]2[C:15](=[CH:16]C=1)[C:14](=[O:18])CC2.CI.[Cl-].[NH4+].[C:23]1([CH3:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(C)(C)C.C(OCC)(=O)C>[CH3:2][O:4][C:25]1[CH:24]=[C:23]2[C:28](=[CH:27][CH:26]=1)[C:14](=[O:18])[C:15]([CH3:16])([CH3:11])[CH2:29]2

Participants

8

Reactant 5

HCID 1140Toluene2×HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 787875-Methoxyindan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 103301582,3-Dihydro-5-methoxy-2,2-dimethyl-1H-inden-1-one

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

7.78 g of potassium t-butoxide was dissolved in 66.3 ml of t-butanol and 150 ml of toluene. Thereafter, 5.00 g of 5-methoxyindanone dissolved in 170 ml of toluene was added dropwise to the reaction solution at room temperature. Approximately 10 minutes later, 4.79 ml of methyl iodide was added to the reaction solution. After completion of the reaction, a saturated ammonium chloride aqueous solution and ethyl acetate were added to the reaction solution, so as to separate an organic layer. The organic layer was then dried over anhydrous magnesium sulfate. After the organic layer had been filtered through celite, the drying agent was removed by filtration. Thereafter, the organic layer was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 2.08 g of 5-methoxy-2,2-dimethylindanone. The obtained product was dissolved in 9 ml of methanesulfonic acid. Then, 2.45 g of methionine was added to the reaction solution, and the obtained mixture was heated to 110° C. After completion of the reaction, a saturated sodium chloride aqueous solution and ethyl acetate were added to the reaction solution, so as to separate an organic layer. The organic layer was then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 1.41 g of the subject compound.

Workup

  1. additionwas added dropwise to the reaction solution at room temperature
  2. customAfter completion of the reaction
  3. customso as to separate an organic layer
  4. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  5. filtrationAfter the organic layer had been filtered through celite
  6. customthe drying agent was removed by filtration
  7. concentrationThereafter, the organic layer was concentrated under a reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f1168b0a92c743e59179787c4a3444bc
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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