Lithium Hydroxide → 3-(4-(Allyloxy)phenyl)-3-(ethoxyimino)propanoic acid

HRID 2243867Notes

Reaction equation

HRID 2243867 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:17][O:18][CH2:19][CH3:20])[CH2:12][C:13]([O:15]C)=[O:14])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[OH-].[Li+]>C1COCC1>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:17][O:18][CH2:19][CH3:20])[CH2:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 72531910Methyl 3-(4-(allyloxy)phenyl)-3-(ethoxyimino)propanoate

Product 1

HCID 725319043-(4-(Allyloxy)phenyl)-3-(ethoxyimino)propanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude methyl 3-(4-(allyloxy)phenyl)-3-(ethoxyimino)propanoate obtained from Step B in THF (7 mL) was added 1 N lithium hydroxide (10.2 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 (10.2 mL) was added. The aqueous layer was extracted with ethyl acetate (×4), 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 (850 mg). 1H NMR (400 MHz, CDCl3) δ 7.58 (2H, d, J=7.6 Hz), 6.89 (2H, d, J=7.6 Hz), 6.02 (1H, m), 5.42 (1H, m), 5.29 (1H, m), 4.54 (1H, m), 4.26 (2H, q, J=5.6 Hz), 3.78 (2H, s), 1.30 (3H, t, J=5.6 Hz).

Workup

  1. customMost of the solvents were removed in vacuo, and 1N hydrochloric acid (10.2 mL)
  2. additionwas added
  3. extractionThe aqueous layer was extracted with ethyl acetate (×4)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-916c46bbe14d4187a77db60453a76cbe
Source dataset
uspto-grants-2010_03
Patent number
US07678784B2

Reaction notes

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