Sodium Hydroxide → 2-Methyl-2-{2-methyl-4-[2-methyl-6-(4-trifluoromethoxy-phenyl)-pyridin-3-ylmethoxy]-phenoxy}-propionic acid

HRID 1242344Notes

Reaction equation

HRID 1242344 reaction equation
C([O:3][C:4](=[O:36])[C:5]([CH3:35])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[C:17]([CH3:33])=[N:18][C:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)=[CH:20][CH:21]=2)=[CH:10][C:9]=1[CH3:34])[CH3:6])C.[OH-].[Na+]>C1COCC1.CCO>[CH3:35][C:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[C:17]([CH3:33])=[N:18][C:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:31])([F:32])[F:30])=[CH:24][CH:23]=3)=[CH:20][CH:21]=2)=[CH:10][C:9]=1[CH3:34])([CH3:6])[C:4]([OH:36])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67072212HCID 67072212, compound

Product 1

HCID 114770492-Methyl-2-{2-methyl-4-[2-methyl-6-(4-trifluoromethoxy-phenyl)-pyridin-3-ylmethoxy]-phenoxy}-propionic acid

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.243 g (0.483 mmol) of the above prepared 2-methyl-2-{2-methyl-4-[2-methyl-6-(4-trifluoromethoxy-phenyl)-pyridin-3-ylmethoxy]-phenoxy}-propionic acid ethyl ester was dissolved in 2.9 ml of THF/EtOH=1/1, treated with 1.45 ml (3 eq.) of 1N NaOH and kept at room temperature for 4 h. The reaction mixture was then poured onto crashed ice/AcOEt/HCl dil., the aqueous phase extracted again with AcOEt; the combined organic layers were washed with water, dried over sodium sulfate, and evaporated to dryness. Recrystallisation from AcOEt/hexane produced finally 0.221 g of the title compound as white solid of mp. 149–151° C.

Workup

  1. additionThe reaction mixture was then poured
  2. extractionthe aqueous phase extracted again with AcOEt
  3. washthe combined organic layers were washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customRecrystallisation from AcOEt/hexane

Sources & evidence

ORD record
ord-5d2ad5c1604d4f41870452bfacd3028c
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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