Sodium Hydroxide → HCID 18801334, compound

HRID 1712931Notes

Reaction equation

HRID 1712931 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:11][C:10]([C:12]([O:14]CC)=[O:13])=[CH:9][CH:8]=1.[OH-].[Na+]>CCO.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 49761854HCID 49761854, compound

Product 1

HCID 18801334HCID 18801334, compoundYield 32.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 5-pyridin-2-yl-2-furoate (2.00 g, 9.21 mmol) in EtOH (10 mL) was added NaOH (0.74 g) in water. The reaction mixture was allowed to stir at rt for 1 h and then concentrated. The residue was diluted with 1M HCl to pH 3-4. A precipitate formed and was collected by filtration and identified as 5-pyridin-2-yl-2-furoic acid (0.41 g). The aqueous solution was extracted with EtOAc. The organic solutions were combined, washed with brine, dried over MgSO4, filtered and concentrated to give additional 5-pyridin-2-yl-2-furoic acid (0.57 g). LCMS: (FA) ES+ 190.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with 1M HCl to pH 3-4
  3. customA precipitate formed
  4. filtrationwas collected by filtration
  5. extractionThe aqueous solution was extracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ddfd43380648485ba934ea2a3098a63a
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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