Sodium Hydroxide → HCID 11744120, compound

HRID 1391813Notes

Reaction equation

HRID 1391813 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([CH:15]([O:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30]C)=[O:29])=[CH:23][CH:22]=3)[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>C1COCC1.CO>[F:33][C:2]([F:1])([F:32])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]([CH:15]([O:20][C:21]3[CH:22]=[CH:23][C:24]([CH2:27][C:28]([OH:30])=[O:29])=[CH:25][CH:26]=3)[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58629943HCID 58629943, compound

Product 1

HCID 11744120HCID 11744120, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl {4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}acetate (329 mg, 0.72 mmol) in THF (9.5 mL) and methanol (9.5 mL) was treated with aqueous NaOH (2M, 9.5 mL) drop-wise and the resulting solution stirred at rt for 17 hours. The volatile solvents were then removed under vacuum and the resulting aqueous mixture acidified with aqueous HCl (2M, 15 mL), diluted with water (100 mL) and the product extracted with DCM (2×100 mL). The combined organic layers were then washed with brine (100 mL), dried (MgSO4), filtered and then reduced under vacuum to give the title compound as a pale yellow foam (314 mg).

Workup

  1. customThe volatile solvents were then removed under vacuum
  2. additiondiluted with water (100 mL)
  3. extractionthe product extracted with DCM (2×100 mL)
  4. washThe combined organic layers were then washed with brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-127eba0a0e6246ddbadabd8b9b3128e6
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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