Sodium Hydroxide → HCID 21935669, compound

HRID 1242361Notes

Reaction equation

HRID 1242361 reaction equation
C([O:3][C:4](=[O:34])[C:5]([CH3:33])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[N:17]=[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[CH3:32])[CH3:6])C.[OH-].[Na+]>C1COCC1.CCO>[CH3:33][C:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[N:17]=[N:18][C:19]([C:22]3[CH:23]=[CH:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=3)=[CH:20][CH:21]=2)=[CH:10][C:9]=1[CH3:32])([CH3:6])[C:4]([OH:34])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67072227HCID 67072227, compound

Product 1

HCID 21935669HCID 21935669, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.183 g (0.386 mmol) of the above prepared 2-methyl-2-{2-methyl-4-[6-(4-trifluoromethyl-phenyl)-pyridazin-3-ylmethoxy]-phenoxy}-propionic acid ethyl ester was dissolved in 8 ml of THF/EtOH=1/1, treated with 1.16 ml (3 eq.) of 1N NaOH and kept at ambient temperature over night. 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, after recrystallisation from hexane/AcOEt, 0.160 g of the title compound as light yellow crystals of mp. 191–192° C.

Workup

  1. waitkept at ambient temperature over night
  2. additionThe reaction mixture was then poured
  3. extractionthe aqueous phase extracted again with AcOEt
  4. washthe combined organic layers were washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customto yield
  8. customafter recrystallisation from hexane/AcOEt, 0.160 g of the title compound as light yellow crystals of mp. 191–192° C.

Sources & evidence

ORD record
ord-58d6b7aafc3b4d17a0fbf82a09062b75
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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