Sodium Hydroxide → HCID 15839729, compound

HRID 864519Notes

Reaction equation

HRID 864519 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+]>O1CCOCC1>[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]([OH: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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10028305HCID 10028305, compound

Product 1

HCID 15839729HCID 15839729, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 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 (3.5 M solution) was treated with 2N sodium hydroxide (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 hydrochloric acid. The resulting milky solution was extracted with ethyl acetate. The ethyl acetate extract was dried over magnesium sulfate and filtered. Solvent removal gave a white solid. The solid was purified by flash chromatography on silica gel eluting with 50% ethyl acetate/hexane, and the resulting solid was crystallized from ethyl acetate and hexane. The desired acid was obtained in 47% yield.

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 ethyl acetate
  5. extractionThe ethyl acetate extract
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. customSolvent removal
  9. customgave a white solid
  10. customThe solid was purified by flash chromatography on silica gel eluting with 50% ethyl acetate/hexane
  11. customthe resulting solid was crystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-255ecff9da6949eca33b89f769617d49
Source dataset
uspto-grants-1996_10
Patent number
US05563164

Reaction notes

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