Dimethyl Sulfide → HCID 20458182, compound

HRID 544729Notes

Reaction equation

HRID 544729 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([N:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)[C:8]([CH3:16])=[CH:7][C:6]=1[CH:17](C)[CH:18]=C)(=O)C.CC(C)=O.[C:25](=[O:27])=[O:26].O=[O+][O-].CSC.[OH-].[K+]>C(Cl)Cl.O.[N+]([O-])([O-])=O.[Ag+]>[OH:4][C:5]1[CH:10]=[C:9]([N:11]2[CH:12]=[CH:13][CH:14]=[CH:15]2)[C:8]([CH3:16])=[CH:7][C:6]=1[CH:17]([CH3:18])[C:25]([OH:27])=[O:26]

Participants

9

Reactant 5

HCID 1068Dimethyl SulfideHCID 14797Potassium HydroxideHCID 24823OzoneHCID 18522661Acetone cardiceHCID 20458181HCID 20458181, compound

Product 1

HCID 20458182HCID 20458182, compound

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.7 g (10 mmoles) of 3-[2-acetoxy-5-methyl-4-(pyrrol-1-yl)-phenyl]-1-butene in 40 ml of absolute methylene chloride is cooled to -78° with acetone/dry ice and ozone is blown through until the blue colour no longer disappears. Then, 2 ml of dimethyl sulphide are added and the cooling bath is removed. The reaction mixture is carefully concentrated in a vacuum rotary evaporator, the residue is dissolved in 50 ml of ethanol, and a solution of 3.7 g (23 mmoles) of silver nitrate in 5 ml of water is added. A solution of 75 ml of a 1 N potassium hydroxide solution is added dropwise to this mixture in the course of approximately 15 minutes. The heterogeneous mixture is further stirred for another 2 hours. The reaction mixture is filtered and the residue is washed with ethanol. The alkaline filtrate is left to stand overnight at room temperature and extracted with methylene chloride. The alkaline solution is cautiously acidified with 6 N hydrochloric acid while cooling and repeatedly extracted with methylene chloride. The organic phases are again washed twice with water, combined, dried over sodium sulphate and concentrated in a vacuum rotary evaporator. Recrystallisation from diisopropyl ether/petroleum ether yields 2-[2-hydroxy-5-methyl-4-(pyrrol-1-yl)phenyl]-propionic acid having a melting point of 73°-74°.

Workup

  1. customthe cooling bath is removed
  2. concentrationThe reaction mixture is carefully concentrated in a vacuum rotary evaporator
  3. dissolutionthe residue is dissolved in 50 ml of ethanol
  4. filtrationThe reaction mixture is filtered
  5. washthe residue is washed with ethanol
  6. waitThe alkaline filtrate is left
  7. waitto stand overnight at room temperature
  8. extractionextracted with methylene chloride
  9. temperaturewhile cooling
  10. extractionrepeatedly extracted with methylene chloride
  11. washThe organic phases are again washed twice with water
  12. dry with materialdried over sodium sulphate
  13. concentrationconcentrated in a vacuum rotary evaporator
  14. customRecrystallisation from diisopropyl ether/petroleum ether

Sources & evidence

ORD record
ord-467d7bd350b54d959c78b916fc8be11d
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Reaction notes

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