Sodium Hydroxide → HCID 53350229, compound

HRID 1627845Notes

Reaction equation

HRID 1627845 reaction equation
[CH3:1][C:2]1[S:26][C:5]2=[N:6][C:7]([CH3:25])=[C:8]([CH:17]([CH2:22][CH2:23][CH3:24])[C:18]([O:20]C)=[O:19])[C:9]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)=[C:4]2[CH:3]=1.[OH-].[Na+]>CO.C(O)C>[CH3:1][C:2]1[S:26][C:5]2=[N:6][C:7]([CH3:25])=[C:8]([CH:17]([CH2:22][CH2:23][CH3:24])[C:18]([OH:20])=[O:19])[C:9]([C:10]3[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=3)=[C:4]2[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66597497HCID 66597497, compound

Product 1

HCID 53350229HCID 53350229, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(2,6-dimethyl-4-p-tolylthieno[2,3-b]pyridin-5-yl)pentanoate (0.135 g; 0.367 mmol) in methanol (8 mL) and ethanol (4 mL) was added a 5% sodium hydroxide solution (10.5 mL; 13.125 mmol). The reaction mixture was heated under reflux for 4.5 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was suspended in water, acidified with 1N HCl (pH˜2) and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was crystallized from a mixture of ethyl acetate/heptane to afford 0.107 g (82%) of the title compound as a white powder.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4.5 h
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was crystallized from a mixture of ethyl acetate/heptane

Sources & evidence

ORD record
ord-93b8ef2553114e3b9e60ee31bc0d0d75
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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