Sodium Hydroxide → HCID 23699208, compound

HRID 741765Notes

Reaction equation

HRID 741765 reaction equation
[C:1]([C:4]1[C:32]([OH:33])=[CH:31][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:27]=[CH:26][C:16]3[CH2:17][CH2:18][CH:19]([C:21]([O:23]CC)=[O:22])[O:20][C:15]=3[C:14]=2[CH2:28][CH2:29][CH3:30])=[C:6]([CH2:34][CH3:35])[CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+:37]>O1CCOCC1.CO>[Na+:37].[C:1]([C:4]1[C:32]([OH:33])=[CH:31][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:27]=[CH:26][C:16]3[CH2:17][CH2:18][CH:19]([C:21]([O-:23])=[O:22])[O:20][C:15]=3[C:14]=2[CH2:28][CH2:29][CH3:30])=[C:6]([CH2:34][CH3:35])[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 10028305HCID 10028305, compound

Product 1

HCID 23699208HCID 23699208, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl 7-[3-(4-acetyl-2-ethyl-5-hydroxyphenoxy)propoxy]-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate in dioxane (3.5M solution) was treated with 2N NaOH (3.0 eqv) and stirred at room temperature. After stirring for 4 hours, the dioxane was removed from the reaction, and the remaining solution was diluted with water and acidified with 5N HCl. The resulting milky solution was extracted with EtOAc. The ethyl acetate extract was dried over MgSO4 and filtered. Solvent removal gave a white solid. The free acid was stirred in methanol and treated with 3 eqv. of NaOH(aq). The solvent was removed from the reaction and the product was purified by CHP-20 reverse phase chromatography eluting with a water/methanol gradient. The pure product was obtained in 68% yield by lyophilization of the product containing fractions.

Workup

  1. stirringAfter stirring for 4 hours
  2. customthe dioxane was removed from the reaction
  3. additionthe remaining solution was diluted with water
  4. extractionThe resulting milky solution was extracted with EtOAc
  5. extractionThe ethyl acetate extract
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered
  8. customSolvent removal
  9. customgave a white solid
  10. customThe solvent was removed from the reaction
  11. customthe product was purified by CHP-20 reverse phase chromatography
  12. washeluting with a water/methanol gradient
  13. customThe pure product was obtained in 68% yield by lyophilization of the product
  14. additioncontaining fractions

Sources & evidence

ORD record
ord-901ed4e05651456f9517d83110cd436e
Source dataset
uspto-grants-1996_09
Patent number
US05552441

Reaction notes

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