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

HRID 1242358Notes

Reaction equation

HRID 1242358 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][CH2:16][C:17]2[C:18]([CH3:33])=[N:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[CH:21][CH:22]=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][CH2:16][C:17]2[C:18]([CH3:33])=[N:19][C:20]([C:23]3[CH:24]=[CH:25][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:27][CH:28]=3)=[CH:21][CH:22]=2)=[CH:10][C:9]=1[CH3:34])([CH3:6])[C:4]([OH:36])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 670724952-Methyl-2-(2-methyl-4-{2-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy]-phenoxy)-propionic acid ethyl ester

Product 1

HCID 219358102-Methyl-2-(2-methyl-4-{2-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy}-phenoxy)-propionic acid

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.070 g (0.140 mmol) of the above prepared 2-methyl-2-(2-methyl-4-{2-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy}-phenoxy)-propionic acid ethyl ester was dissolved in 0.84 ml of THF/EtOH=1/1, treated with 0.42 ml (3 eq.) of 1N NaOH and kept at ambient 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 to yield 0.057 g of the title product as light yellow foam.

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

Sources & evidence

ORD record
ord-77f469c6101c4736b751a72fa4fccab9
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

Loading…