Sodium Hydroxide → HCID 15839729, compound

HRID 1110080Notes

Reaction equation

HRID 1110080 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 (3.5M 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 HC1. 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 solid was purified by flash chromatography on silica gel eluting with 50% EtOAc/Hexane, and the resulting solid was crystallized from EtOAc 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 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 solid was purified by flash chromatography on silica gel eluting with 50% EtOAc/Hexane
  11. customthe resulting solid was crystallized from EtOAc and hexane

Sources & evidence

ORD record
ord-f7b3dbbce16e49b580eebe836b8f306d
Source dataset
uspto-grants-1994_06
Patent number
US05324743

Reaction notes

Loading…