Sodium Hydroxide → HCID 21935920, compound

HRID 1242337Notes

Reaction equation

HRID 1242337 reaction equation
C([O:3][C:4](=[O:35])[C:5]([CH3:34])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[C:17]([CH3:32])=[N:18][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[CH:20][CH:21]=2)=[CH:10][C:9]=1[CH3:33])[CH3:6])C.[OH-].[Na+]>C1COCC1.CCO>[CH3:34][C:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[C:17]([CH3:32])=[N:18][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:24][CH:23]=3)=[CH:20][CH:21]=2)=[CH:10][C:9]=1[CH3:33])([CH3:6])[C:4]([OH:35])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67072487HCID 67072487, compound

Product 1

HCID 21935920HCID 21935920, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.221 g (0.453 mmol) of the above prepared 2-methyl-2-{2-methyl-4-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethoxy]-phenoxy}-propionic acid ethyl ester was dissolved in 2.7 ml of THF/EtOH=1/1, treated with 1.35 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. Recrystallisation from AcOEt/hexane afforded finally 0.194 g of the title compound as white solid of mp. 164–165° 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-617b90d602ae4a5a842073b32a097766
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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