Sodium Hydroxide → 5-pyridin-2-ylpentanoic Acid

HRID 499581Notes

Reaction equation

HRID 499581 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]CC)=[O:12].[OH-].[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11241218Ethyl 5-(pyridin-2-yl)pentanoate

Product 1

HCID 112523245-pyridin-2-ylpentanoic AcidYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5-(2-pyridyl)valerate (3.6 g, 17.2 mmol) was dissolved in ethanol (12 ml), and 2 M aqueous sodium hydroxide solution (12.9 ml, 25.8 mmol) was added thereto. The reaction mixture was stirred at room temperature for 1.5 hrs. The solvent was evaporated, and the residue was combined with ethanol and filtered to remove the insolubles. The filtrate was concentrated to give the titled compound (2.5 g, 82%)

Workup

  1. customThe solvent was evaporated
  2. filtrationfiltered
  3. customto remove the insolubles
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c8e72c11db444f7f9ecb01693fdd5bcc
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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