Sodium Hydroxide → (Z)-2-Ethoxy-3-[2-methyl-4-(5-methyl-2-o-tolyl-oxazol-4-ylmethoxy)-phenyl]-acrylic acid

HRID 1064886Notes

Reaction equation

HRID 1064886 reaction equation
C([O:3][C:4](=[O:32])/[C:5](/[O:29][CH2:30][CH3:31])=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])[O:18][C:19]=2[CH3:20])=[CH:9][C:8]=1[CH3:28])C.[OH-].[Na+]>C1COCC1.CO>[CH2:30]([O:29]/[C:5](=[CH:6]\[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])[O:18][C:19]=2[CH3:20])=[CH:9][C:8]=1[CH3:28])/[C:4]([OH:32])=[O:3])[CH3:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69282190(Z)-2-ethoxy-3-[2-methyl-4-(5-methyl-2-o-tolyl-oxazol-4-ylmethoxy)-phenyl]-acrylic acid ethyl ester

Product 1

HCID 22273871(Z)-2-Ethoxy-3-[2-methyl-4-(5-methyl-2-o-tolyl-oxazol-4-ylmethoxy)-phenyl]-acrylic acidYield 99.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of (Z)-2-ethoxy-3-[2-methyl-4-(5-methyl-2-o-tolyl-oxazol-4-ylmethoxy)-phenyl]-acrylic acid ethyl ester (6.8 g, 15.6 mmol) in THF/methanol 2/1 (102 ml) was added a 3 M aqueous NaOH solution (26 ml, 78 mmol). The reaction mixture was stirred for 3 h at ambient temperature, concentrated under reduced pressure, diluted with ice water and acidified with with 1 M aqueous HCl solution. Twofold extraction with ethyl acetate was followed by washing of the combined extracts with ice water/brine 1/1 (three times) and drying of the organic layer over sodium sulfate. The solvent was removed under reduced pressure and the crude product crystallized from dichloromethane/n-heptane to give the title compound (6.3 g, 15.5 mmol, 99%) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with ice water
  3. extractionTwofold extraction with ethyl acetate
  4. washby washing of the combined extracts with ice water/brine 1/1 (three times)
  5. dry with materialdrying of the organic layer over sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe crude product crystallized from dichloromethane/n-heptane

Sources & evidence

ORD record
ord-cac06ce30e4848438ea61789e5dd0961
Source dataset
uspto-grants-2005_11
Patent number
US06969725B2

Reaction notes

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