Sodium Hydroxide → HCID 21935708, compound

HRID 1242340Notes

Reaction equation

HRID 1242340 reaction equation
C([O:3][C:4](=[O:36])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[C:18]([CH3:34])=[N:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[C:25]([F:33])[CH:24]=3)=[CH:21][CH:22]=2)=[CH:11][C:10]=1[CH3:35])([CH3:7])[CH3:6])C.[OH-].[Na+]>C1COCC1.CCO>[F:33][C:25]1[CH:24]=[C:23]([C:20]2[N:19]=[C:18]([CH3:34])[C:17]([CH2:16][O:15][C:12]3[CH:13]=[CH:14][C:9]([O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:36])=[O:3])=[C:10]([CH3:35])[CH:11]=3)=[CH:22][CH:21]=2)[CH:28]=[CH:27][C:26]=1[C:29]([F:31])([F:32])[F:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67072404HCID 67072404, compound

Product 1

HCID 21935708HCID 21935708, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.214 g (0.423 mmol) of the above prepared 2-{4-[6-(3-fluoro-4-trifluoromethyl-phenyl)-2-methyl-pyridin-3-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester was dissolved in 0.85 ml of THF/EtOH=1/1, treated with 1.27 ml (3 eq.) of 1N NaOH and kept at ambient temperature for 2 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 and brine, dried over magnesium sulfate, and evaporated to dryness. Recrystallisation from AcOEt/hexane yielded finally 0.191 g of the title compound as white crystals of mp. 175–76°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 and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customRecrystallisation from AcOEt/hexane

Sources & evidence

ORD record
ord-ee32f9329c7941bdaa21ff93f778de4d
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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