Sodium Hydroxide → ({2-Methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}hexyl)oxy]phenyl}oxy)acetic acid

HRID 1391816Notes

Reaction equation

HRID 1391816 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)[N:16]=2)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:5]=[CH:4][C:3]=1[O:31][CH2:32][C:33]([O:35]CC)=[O:34].[OH-].[Na+]>CO.C1COCC1>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=3)[N:16]=2)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:5]=[CH:4][C:3]=1[O:31][CH2:32][C:33]([OH:35])=[O:34]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58629912Ethyl ({2-methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}hexyl)oxy]phenyl}oxy)acetate

Product 1

HCID 10368182({2-Methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}hexyl)oxy]phenyl}oxy)acetic acidYield 73.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl ({2-methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}hexyl)oxy]phenyl}oxy)acetate (80 mg, 0.16 mmol) in MeOH (2 mL) and THF (2 mL) at rt was added aqueous NaOH (2M, 1 mL, 2.0 mmol) and the resulting mixture stirred for 2.5 hours. The solvents were then removed under vacuum and the residue partitioned between DCM (20 mL) and aqueous HCl (2M, 20 mL), the layers separated and the aqueous re-extracted with DCM (20 mL). The combined organic solution was passed through a hydrophobic frit and then reduced affording the title compound as colourless oil (57 mg).

Workup

  1. customThe solvents were then removed under vacuum
  2. customthe residue partitioned between DCM (20 mL) and aqueous HCl (2M, 20 mL)
  3. customthe layers separated
  4. extractionthe aqueous re-extracted with DCM (20 mL)

Sources & evidence

ORD record
ord-c0f1acfa465243c3991bb2dc88780579
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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