Hydrochloric Acid → 2-(2-(6-Methoxy-1-benzofuran-5-yl)ethoxy)acetic acid

HRID 7461Notes

Reaction equation

HRID 7461 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH2:12][CH2:13][OH:14])=[CH:10][C:6]2[CH:7]=[CH:8][O:9][C:5]=2[CH:4]=1.C[C:16]([CH3:19])([O-:18])C.[K+].[OH2:21].Cl>C(O)(C)(C)C.CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:11]([CH2:12][CH2:13][O:14][CH2:19][C:16]([OH:21])=[O:18])=[CH:10][C:6]2[CH:7]=[CH:8][O:9][C:5]=2[CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21990154HCID 21990154, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 219900752-(2-(6-Methoxy-1-benzofuran-5-yl)ethoxy)acetic acid

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a mixture of 7.0 mL of tert-butanol and 1.75 mL of N,N-dimethylformamide was dissolved 1.75 g of 2-(6-methoxy-1-benzofuran-5-yl)-1-ethanol, and 2.2 g of 1-chloroacetylpiperidine and 1.54 g of potassium tert-butoxide were added to the solution under ice-cooling, after which the resulting mixture was stirred at the same temperature for 30 minutes and then at the room temperature for 2 hours. Water and ethyl acetate were added to the reaction mixture and the pH was adjusted to 1 with 6 mol/L hydrochloric acid, after which the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was dissolved in 10.5 mL of a 90% aqueous ethanol solution, followed by adding thereto 0.91 g of sodium hydroxide, and the resulting mixture was heated under reflux for 3 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the pH was adjusted to 1 with 6 mol/L hydrochloric acid, after which the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. Diisopropyl ether was added to the residue, and the crystals precipitated were collected by filtration, washed with diisopropyl ether and then dried to obtain 1.42 g of 2-[2-(6-methoxy-1-benzofuran-5-yl)ethoxy]acetic acid as yellow crystals.

Workup

  1. additionwere added to the solution under ice-
  2. temperaturecooling
  3. waitat the room temperature for 2 hours
  4. customafter which the organic layer was separated
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. dissolutionThe residue was dissolved in 10.5 mL of a 90% aqueous ethanol solution
  10. additionby adding
  11. temperature0.91 g of sodium hydroxide, and the resulting mixture was heated
  12. temperatureunder reflux for 3 hours
  13. temperatureAfter the reaction mixture was cooled
  14. additionwater and ethyl acetate were added
  15. customafter which the organic layer was separated
  16. washThe organic layer was washed with water
  17. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  18. distillationdistilled under reduced pressure
  19. customto remove the solvent
  20. additionDiisopropyl ether was added to the residue
  21. customthe crystals precipitated
  22. filtrationwere collected by filtration
  23. washwashed with diisopropyl ether
  24. customdried

Sources & evidence

ORD record
ord-fc55f392ceb0476c8a806ab8be985509
Source dataset
uspto-grants-2006_08
Patent number
US07087594B2

Reaction notes

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