Ethanol → 3-hydroxy-3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]propanoic acid

HRID 922332Notes

Reaction equation

HRID 922332 reaction equation
[OH:1][CH:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23]/[C:24](=[N:31]\[O:32][CH3:33])/[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)[CH2:3][C:4]([O:6]C)=[O:5].C1COCC1.C(O)C.[OH-].[Na+]>O>[OH:1][CH:2]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23]/[C:24](=[N:31]\[O:32][CH3:33])/[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:18][CH:17]=2)=[CH:12][CH:13]=1)[CH2:3][C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 87106283methyl 3-hydroxy-3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]propanoate

Product 1

HCID 871062843-hydroxy-3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]propanoic acidYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirring solution of methyl 3-hydroxy-3-{4-[(4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}benzyl)oxy]phenyl}propanoate (0.015 g, 0.0334 mmol) in the mixture of THF and Ethanol was added NaOH (0.003 g, 0.075 mmol) in 0.5 mL of water at 0° C., then stirred at RT for 2 h. After the completion of the SM reaction mass was concentrated under vacuum to remove solvents and diluted with water. Aqueous portion was neutralized with 1N HCl up to neutral pH, then extracted with ethyl acetate organic layer was washed with water and brine, dried over anhydrous Na2SO4. Evaporation under vacuum yields the titled compound as white solid (0.008 g, yield: 13.70%). Purity: 96.8%.

Workup

  1. customAfter the completion of the SM reaction mass
  2. concentrationwas concentrated under vacuum
  3. customto remove solvents
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate organic layer
  6. washwas washed with water and brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customEvaporation under vacuum

Sources & evidence

ORD record
ord-5f5fdf0009614d7aa283a24f84e4b0ed
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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