Methanol → {[6-(1-Benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetic acid

HRID 456828Notes

Reaction equation

HRID 456828 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=[C:9]1[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([O:29][CH2:30][C:31]([O:33]C)=[O:32])[CH:23]=[CH:22]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C1COCC1.CO>O>[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:11][CH:10]=[C:9]1[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([O:29][CH2:30][C:31]([OH:33])=[O:32])[CH:23]=[CH:22]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86603526Methyl {[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetate

Product 1

HCID 11517668{[6-(1-Benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl {[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetate (0.250 g, 0.559 mmol), prepared in the previous step, and 1N NaOH (0.84 mL, 0.84 mmol) in 1:1:1 THF:MeOH:water (30 mL) was stirred at ambient temperature for 10 minutes. The volatiles were removed under reduced pressure (without the application of heat). The residue was partitioned between 0.1N HCl and EtOAc. The layers were separated and the aqueous layer was extracted one time with EtOAc. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give the title compound as a pale-yellow solid (0.23 g, 95%), mp 171–172° C. Elemental Analysis for C29H23NO3.0.17 H2O Calc'd: C, 79.79; H, 5.39; N, 3.21. Found: C, 79.88; H, 5.37; N, 2.96.

Workup

  1. customThe volatiles were removed under reduced pressure (without the application
  2. temperatureof heat)
  3. customThe residue was partitioned between 0.1N HCl and EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted one time with EtOAc
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-71f48e32e13542c0b7a31bed2025ccb8
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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