Thiophenol → 2-[1-(Phenylsulfanyl)cyclobutyl]acetic acid

HRID 1175762Notes

Reaction equation

HRID 1175762 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[C:14]1(=[CH:18][C:19]([OH:21])=[O:20])[CH2:17][CH2:16][CH2:15]1>C1COCC1.CN(C=O)C>[C:1]1([S:7][C:14]2([CH2:18][C:19]([OH:21])=[O:20])[CH2:17][CH2:16][CH2:15]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 219231732-Cyclobutylideneacetic acid2×

Product 1

HCID 667456062-[1-(Phenylsulfanyl)cyclobutyl]acetic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of thiophenol (70 mmol) in THF (10 ml) was refluxed for 1 h in the presence of K2CO3 (70 mmol) as a base. A solution of Cyclobutylidene acetic acid (intermediate 1) (35 mmol) in DMF (1.0 ml) was added to the above reaction. The reaction was monitored by TLC for completion. After 3 days the reaction was cooled and filtered. It was then neutralized with ethyl acetate saturated with hydrochloric acid and the compound was extracted with ethyl acetate. Organic layer was then separated, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was column purified to give the compound as a yellow solid.

Workup

  1. temperatureAfter 3 days the reaction was cooled
  2. filtrationfiltered
  3. extractionthe compound was extracted with ethyl acetate
  4. customOrganic layer was then separated
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under vacuum
  7. custompurified

Sources & evidence

ORD record
ord-0984d359dff543baa7f3ce6e2cb3af33
Source dataset
uspto-grants-2010_11
Patent number
US07842703B2

Reaction notes

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