Potassium Carbonate → HCID 59746918, compound

HRID 2039806Notes

Reaction equation

HRID 2039806 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][C:3]=1[O:12][CH3:13].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CC(C)=O>[CH3:13][O:12][C:3]1[CH:4]=[C:5]2[C:9]([C:8](=[O:11])[CH2:7][CH2:6]2)=[CH:10][C:2]=1[O:1][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 2331486-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 59746918HCID 59746918, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 6-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one 18a (0.01 mol, 1.78 g) in acetone (50 ml) was added potassium carbonate (0.02 mol, 2.80 g). The resulting mixture was refluxed for 2 hours. After cooling to room temperature ethyl 4-bromobutyrate was added. The reaction mixture was stirred at 60° C. for 12 h. The progress of the reaction was monitored by TLC. The reaction mixture was filtered and the precipitate was washed with acetone (15 ml×2). The combined filtrate was concentrated on rotavapor and the residue was diluted with ethyl acetate. The ethyl acetate solution was successively washed with water, saturated sodium bicarbonate (Na2HCO3), water and dried over magnesium sulfate (Mg2SO4). After evaporation of the solvent the crude product was purified by passing through a short silica gel column using 0-50% gradient of ethyl acetate and hexane as eluent to give the pure indanone as colorless thick liquid in 30% yield (0.87 g). 1H NMR (400 MHz, CDCl3): δ 1.21 (3H, broad t); 2.16 (2H, m); 2.44 (2H, m); 2.59 (2H, m); 2.96 (2H, m); 3.93 (3H, s); 4.04 (2H, broad t); 4.10 (2H, broad q); 6.84 (1H, m); 7.43 (1H, s); 7.12 (1H, s). MS (ESI): m/z=293.20 (M+H+).

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hours
  2. additionwas added
  3. filtrationThe reaction mixture was filtered
  4. washthe precipitate was washed with acetone (15 ml×2)
  5. concentrationThe combined filtrate was concentrated on rotavapor
  6. additionthe residue was diluted with ethyl acetate
  7. washThe ethyl acetate solution was successively washed with water, saturated sodium bicarbonate (Na2HCO3), water
  8. dry with materialdried over magnesium sulfate (Mg2SO4)
  9. customAfter evaporation of the solvent the crude product
  10. customwas purified

Sources & evidence

ORD record
ord-fc2478e9050d45f283c88a34ce974eea
Source dataset
uspto-grants-2013_11
Patent number
US08580822B2

Reaction notes

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