Potassium Carbonate → HCID 60155351, compound

HRID 1506863Notes

Reaction equation

HRID 1506863 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:14])[C:10]([O:12]C)=[O:11].C(=O)([O-])[O-].[K+].[K+].Cl[CH:22]1[CH2:26][CH2:25][CH2:24][C:23]1=[O:27]>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH:22]2[CH2:26][CH2:25][CH2:24][C:23]2=[O:27])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:14])[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127512-ChlorocyclopentanoneHCID 58415206HCID 58415206, compound

Product 1

HCID 60155351HCID 60155351, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound (8) obtained above (0.87 g, 4.4 mmol) in dry DMF (8.7 mL), potassium carbonate and chlorocyclopentanone (0.53 mL, 5.3 mmol) were added, and the obtained mixture was heated to reflux for 3 hours. After the reaction, the mixture was filtered and the obtained filtrate was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (7:1) solution followed by conventional hydrolysis to give 0.28 g (32%) of compound (12) of interest as yellow oil.

Workup

  1. temperaturethe obtained mixture was heated
  2. temperatureto reflux for 3 hours
  3. customAfter the reaction
  4. filtrationthe mixture was filtered
  5. distillationthe obtained filtrate was distilled off under reduced pressure
  6. washThe residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (7:1) solution
  7. customfollowed by conventional hydrolysis

Sources & evidence

ORD record
ord-c2326dc2d8894c40ac1feaaf5233acf4
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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