Sodium Hydroxide → HCID 11519845, compound

HRID 456845Notes

Reaction equation

HRID 456845 reaction equation
[C:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[C:10]([C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[CH:29]=[C:28]([O:33][CH2:34][C:35]3[CH:44]=[CH:43][C:38]([C:39]([O:41]C)=[O:40])=[CH:37][CH:36]=3)[CH:27]=[CH:26]4)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1.CO.O>[C:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=3)[C:10]([C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[CH:29]=[C:28]([O:33][CH2:34][C:35]3[CH:36]=[CH:37][C:38]([C:39]([OH:41])=[O:40])=[CH:43][CH:44]=3)[CH:27]=[CH:26]4)=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 18439048HCID 18439048, compound

Product 1

HCID 11519845HCID 11519845, compoundYield 95.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-{[(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]methyl}benzoate (200 mg, 0.338 mmol), prepared in the previous step, and 1 N NaOH (507 μL, 0.507 mmol) in 20 mL of THF plus 20 mL of methanol plus 5 mL water was refluxed under nitrogen for 9 h. The reaction was filtered and then allowed to cool to room temperature. The reaction was acidified by the addition of 2.5 mL of 1 N HCl and then concentrated under reduced pressure to remove the THF and methanol. The residue was diluted with water. The solid formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (186 mg, 95%) as an off-white solid, mp 228–229° C. Elemental Analysis for C36H26F3NO3.0.15 H2O.0.04 C4H8O Calc'd: C, 74.47; H, 4.60; N, 2.40. Found: C, 74.52; H, 4.49; N, 2.68.

Workup

  1. temperaturewas refluxed under nitrogen for 9 h
  2. filtrationThe reaction was filtered
  3. additionThe reaction was acidified by the addition of 2.5 mL of 1 N HCl
  4. concentrationconcentrated under reduced pressure
  5. customto remove the THF and methanol
  6. additionThe residue was diluted with water
  7. customThe solid formed
  8. filtrationwas collected by filtration
  9. washrinsed with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-e414e4c4ef5a498da95c207237cebf11
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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