Sodium Hydroxide → 2-Methoxy-3-(4-(2-(5-methyl-2-phenyloxazol-4-yl)ethoxy)naphthalen-1-yl)propanoic acid

HRID 479121Notes

Reaction equation

HRID 479121 reaction equation
C([O:3][C:4](=[O:34])[CH:5]([O:32][CH3:33])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C1COCC1.CCO>[CH3:33][O:32][CH:5]([CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])=[CH:9][CH:8]=1)[C:4]([OH:34])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 695574422-Methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester

Product 1

HCID 180034462-Methoxy-3-(4-(2-(5-methyl-2-phenyloxazol-4-yl)ethoxy)naphthalen-1-yl)propanoic acidYield 59.1%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.137 g of 2-Methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester (0.298 mmol) was dissolved in 2 ml of THF/EtOH=1/1 and treated with 0.745 ml of 2N NaOH. The reaction mixture was kept for 24 h at ambient temperature and then quenched by pouring onto crashed ice/HCl. Twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents left a crude product, which was purified by twofold crystallisation from AcOEt/hexane to yield 0.076 g of the title compound as a white solid, mp.128-130°.

Workup

  1. customquenched
  2. additionby pouring
  3. extractionTwofold extraction with AcOEt
  4. washwashing with water
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  6. waitleft a crude product, which
  7. customwas purified by twofold crystallisation from AcOEt/hexane

Sources & evidence

ORD record
ord-7f556134d3ce45278259cfee1a770e44
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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