Sulfuric Acid → 5-(2-Fluoro-4-biphenylyl)-4-oxohexanoic acid

HRID 256776Notes

Reaction equation

HRID 256776 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:23])[C:9](=[O:22])[CH2:10][CH:11](C(OCC)=O)[C:12]([O:14]CC)=[O:13])[CH:5]=[CH:4][C:3]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.S(=O)(=O)(O)O>C(O)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:23])[C:9](=[O:22])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:4][C:3]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 19785556Diethyl 2-(3-(2-fluoro-4-biphenylyl)-2-oxobutyl)malonate

Product 1

HCID 197855665-(2-Fluoro-4-biphenylyl)-4-oxohexanoic acidYield 54%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of diethyl 2-(3-(2-fluoro-4-biphenylyl)-2-oxobutyl)malonate (5.00 g, 12.5 mmoles), acetic acid (100 ml), and 30% sulfuric acid (100 ml) was heated under reflux for 4 hours. After cooling the reaction mixture was extracted with ether. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure The mixture of the residue, ethanol (100 ml) and concentrated sulfuric acid (1.0 g) was heated at 50° C. for 3 hours. The reaction mixture was concentrated under reduced pressure and the residue was extracted with ether. The organic layer was washed successively with water, aqueous sodium bicarbonate and water, dried over sodium sulfate and concentrated under reduced pressure. Purification of the residue by medium pressure silica gel column chromatography gave the desired 5-(2-fluoro-4-biphenylyl)-4-oxohexanoic acid (2.21 g, 6.71 mmoles, yield 54%) as a light yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling the reaction mixture
  4. extractionwas extracted with ether
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionThe mixture of the residue, ethanol (100 ml) and concentrated sulfuric acid (1.0 g)
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. extractionthe residue was extracted with ether
  11. washThe organic layer was washed successively with water, aqueous sodium bicarbonate and water
  12. dry with materialdried over sodium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customPurification of the residue by medium pressure silica gel column chromatography

Sources & evidence

ORD record
ord-0b5cb571e7dc4a5d9c8111adbf6c6bdd
Source dataset
uspto-grants-1993_11
Patent number
US05258396

Reaction notes

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