HCID 67257520, compound → 4,5-Dihydro-4-(nitromethyl)cyclopenta[b]thiophen-6-one

HRID 2371037Notes

Reaction equation

HRID 2371037 reaction equation
[N+:1]([CH2:4][CH:5]([C:10]1[CH:14]=[CH:13][S:12][CH:11]=1)[CH2:6][C:7]([OH:9])=O)([O-:3])=[O:2]>ClCCCl>[N+:1]([CH2:4][CH:5]1[C:10]2[CH:14]=[CH:13][S:12][C:11]=2[C:7](=[O:9])[CH2:6]1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 67257520HCID 67257520, compound

Product 1

HCID 672578934,5-Dihydro-4-(nitromethyl)cyclopenta[b]thiophen-6-oneYield 74%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-nitro-3-(thiophen-3-yl)butanoic acid (3.4 g, 15.9 mmol) in DCE (20 mL) was added PPA (20 g) and the resulting mixture was refluxed overnight. After concentration, the reaction mixture was treated with solid NaOH, followed by addition of water. After stirring for 30 minutes, the mixture was extracted with DCM. The DCM extract was washed with brine and dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (2.3 g, 74%).

Workup

  1. temperaturethe resulting mixture was refluxed overnight
  2. concentrationAfter concentration
  3. additionthe reaction mixture was treated with solid NaOH
  4. additionfollowed by addition of water
  5. extractionthe mixture was extracted with DCM
  6. extractionThe DCM extract
  7. washwas washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationAfter filtration and concentration
  10. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-95d89e2124164fc4a1f542df3484a2a2
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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