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

HRID 922184Notes

Reaction equation

HRID 922184 reaction equation
CO.C1COCC1.C[O:9][C:10](=[O:39])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29](=[N:36][O:37][CH3:38])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:23][CH:22]=2)=[CH:15][CH:14]=1.[OH-].[Na+]>O>[CH3:38][O:37]/[N:36]=[C:29](/[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)\[CH2:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][C:10]([OH:39])=[O:9])=[CH:14][CH:15]=2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 866957263-{4-[4-(2-Methoxyimino-2-phenyl-ethoxy)-benzyloxy]-phenyl}-propanoic acid methyl ester

Product 1

HCID 565935553-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]propanoic acidYield 63.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 25 mL RB flask fitted with magnetic stirrer was charged 2 mL of methanol and 1 mL of THF. To the stirred solvent, was added 3-{4-[4-(2-methoxyimino-2-phenyl-ethoxy)-benzyloxy]-phenyl}-propanoic acid methyl ester (0.085 g, 0.19 mmol). To the stirred solution, NaOH (0.015 g, 0.375 mmol) in water (1 mL) was added. The resulting solution was stirred at RT for 3 h. After completion of the reaction (reaction monitored by TLC), the solvent was evaporated under reduced pressure. The RM was diluted with 1 mL of water, cooled to 0° C., then acidified with 1N HCl (5 mL), and extracted with ethyl acetate (10 mL×2), organic layer was given water (5 mL) and saturated brine solution wash (5 mL), dried over anhydrous Na2SO4 and evaporated to dryness to yield colorless solid (0.050 g, yield: 63.3%); purity: 97.65%.

Workup

  1. customTo a 25 mL RB flask fitted with magnetic stirrer
  2. customAfter completion of the reaction (reaction monitored by TLC)
  3. customthe solvent was evaporated under reduced pressure
  4. additionThe RM was diluted with 1 mL of water
  5. temperaturecooled to 0° C.
  6. extractionextracted with ethyl acetate (10 mL×2), organic layer
  7. washwash (5 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-dad364399a164acbb9b1e8fb84587b8b
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

Loading…