Sodium Hydroxide → HCID 66597499, compound

HRID 1627843Notes

Reaction equation

HRID 1627843 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[C:3]=1[CH3:27].[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[C:3]=1[CH3:27]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide3×HCID 66597488HCID 66597488, compound

Product 1

HCID 66597499HCID 66597499, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(2,3,6-trimethyl-4-p-tolylthieno[2,3-b]pyridin-5-yl)pentanoate (0.074 g; 0.194 mmol) in methanol (4 mL) and ethanol (2 mL) was added a 5% sodium hydroxide solution (2 mL; 2.50 mmol). The reaction mixture was heated under reflux for 2 h. 5% sodium hydroxide solution (2 mL; 2.500 mmol) was added again and reflux was maintained for 2 h. 5% Sodium hydroxide solution (1 mL; 1.250 mmol) was added. After 3 h at reflux, 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 0.037 g (52%) of the title compound as a white powder.

Workup

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

Sources & evidence

ORD record
ord-6ef67e9ba7ce4a5aadea748969d5058a
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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