Sodium Hydroxide → HCID 10160327, compound

HRID 2260850Notes

Reaction equation

HRID 2260850 reaction equation
[CH2:1]([C:3]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[C:24]([O:34]CC2C=CC=CC=2)=[CH:23][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])[CH3:2].[OH-].[Na+]>C(O)C.Cl>[CH2:1]([C:3]1[CH:26]=[C:25]([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)[C:24]([OH:34])=[CH:23][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19419244HCID 19419244, compound

Product 1

HCID 10160327HCID 10160327, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 375 mg of ethyl 3-(2-(3-(2-ethyl-4-(4-fluorophenyl)-5-benzyloxyphenoxy)propoxy)phenyl)propionate in 25 ml of ethanol was mixed with 5 ml of 5.0N sodium hydroxide and stirred 16 hours. The mixture was diluted with 1.0N hydrochloric acid and extracted with 3:1 dichloromethane/isopropanol. The organic phase was washed with saturated sodium chloride, dried over sodium sulfate, and evaporated in vacuo providing the desired 3-(2-(3-(2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy)propoxy)phenyl)propionic acid in 93% yield. NMR.

Workup

  1. extractionextracted with 3:1 dichloromethane/isopropanol
  2. washThe organic phase was washed with saturated sodium chloride
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-e93e30277f3c476e831bdccfecb0b9ae
Source dataset
uspto-grants-1995_12
Patent number
US05478857

Reaction notes

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