Lithium Hydroxide → 3-(Methoxyimino)-3-(4-methoxyphenyl)propanoic acid

HRID 133789Notes

Reaction equation

HRID 133789 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH2:5][C:6]([O:8]CC)=[O:7].[OH-].[Li+]>C1COCC1>[CH3:1][O:2][N:3]=[C:4]([C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)[CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58984518Ethyl 3-(methoxyimino)-3-(4-methoxyphenyl)propanoate

Product 1

HCID 589845323-(Methoxyimino)-3-(4-methoxyphenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(methoxyimino)-3-(4-methoxyphenyl)propanoate from Step A in THF (5 mL) was added 1 N lithium hydroxide (5 mL), and the resulting solution was stirred at room temperature for 12 h. Most of the solvents were removed in vacuo, and 1N hydrochloric acid (5 mL) was added. The aqueous layer was extrated with ethyl acetate (x4), and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo to give the title compound as a white solid (350 mg). 1H NMR (400 MHz, CDCl3) δ 7.58 (m), 6.89 (m), 4.00 (s), 3.96 (3), 3.81 (s), and 3.78 (s).

Workup

  1. customMost of the solvents were removed in vacuo, and 1N hydrochloric acid (5 mL)
  2. additionwas added
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-7040cc2b665f4e909153f74ea3074a02
Source dataset
uspto-grants-2008_06
Patent number
US07390925B2

Reaction notes

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