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

HRID 922327Notes

Reaction equation

HRID 922327 reaction equation
CO.C1COCC1.[OH:8][CH:9]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30]/[C:31](=[N:38]\[O:39][CH3:40])/[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:25][CH:24]=2)=[CH:17][CH:16]=1)[CH2:10][C:11]([O:13]C)=[O:12].[OH-].[Na+]>O>[OH:8][CH:9]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30]/[C:31](=[N:38]\[O:39][CH3:40])/[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:25][CH:24]=2)=[CH:19][CH:20]=1)[CH2:10][C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 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 52.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 25 mL RB flask fitted with magnetic stirrer was charged 2 mL of Methanol and 2 mL of THF. To the stirred solvent was added methyl 3-hydroxy-3-{4-[(4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}benzyl)oxy]phenyl}propanoate (0.04 g, 0.08 mmol) and NaOH was added followed by water (0.5 mL). Then it was stirred at RT for 12 h, after completion of the reaction (reaction monitored by TLC), reaction mixture was evaporated completely and the crude was washed with ether, and diluted with water and then neutralized with 1N HCl, then extracted with ethyl acetate, organic layer was washed with water and brine, dried over Na2SO4. The organic layer was evaporated on rotavapor under reduced pressure to give the product as a white colour solid. (0.02 g, yield: 52.6%); Purity: 45.3% and 43.6%.

Workup

  1. customTo a 25 mL RB flask fitted with magnetic stirrer
  2. additionwas added
  3. customafter completion of the reaction (reaction monitored by TLC), reaction mixture
  4. customwas evaporated completely
  5. washthe crude was washed with ether
  6. additiondiluted with water
  7. extractionextracted with ethyl acetate, organic layer
  8. washwas washed with water and brine
  9. dry with materialdried over Na2SO4
  10. customThe organic layer was evaporated on rotavapor under reduced pressure
  11. customto give the product as a white colour solid

Sources & evidence

ORD record
ord-47b7c9d3c8cc435ca058ddd5438d8e89
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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