Potassium Carbonate → 4-Propoxy-2,3-dihydro-1H-inden-1-one

HRID 2377230Notes

Reaction equation

HRID 2377230 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].C(=O)([O-])[O-].[K+].[K+].[CH2:18](I)[CH2:19][CH3:20]>CC(C)=O>[CH2:18]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11])[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 607305354-Propoxy-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 4-hydroxy-1-indanone (1.0 g, 6.75 mmol) in acetone (30 mL) was added potassium carbonate (2.8 g, 20.24 mmol) and propyl iodide (0.72 mL, 7.42 mmol) and the reaction mixture was heated to reflux for about 7 hours. The reaction was cooled, concentrated under vacuum and partitioned between water and dichloromethane. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried (Na2SO4), filtered and concentrated under vacuum and the residue was purified by flash column chromatography on silica gel using dichloromethane as the mobile phase to provide the desired product. MS (APCI): m/z 191 (M+H)+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for about 7 hours
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated under vacuum
  5. custompartitioned between water and dichloromethane
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with dichloromethane
  8. dry with materialThe combined organic extracts were dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customthe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-ec3b8374dd3449449c3f4a7692d3875b
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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