Tetrahydrofuran → (2-(6-Fluoro-1-methyl-3-indolyl)-6-benzoxazolyl)acetic acid

HRID 1372761Notes

Reaction equation

HRID 1372761 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[O:13][C:14]4[CH:20]=[C:19]([CH2:21][C:22]([O:24]C)=[O:23])[CH:18]=[CH:17][C:15]=4[N:16]=3)=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.C1COCC1.[OH-].[Na+]>Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[O:13][C:14]4[CH:20]=[C:19]([CH2:21][C:22]([OH:24])=[O:23])[CH:18]=[CH:17][C:15]=4[N:16]=3)=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58778430Methyl (2-(6-fluoro-1-methyl-3-indolyl)-6-benzoxazolyl)acetate

Product 1

HCID 17859002(2-(6-Fluoro-1-methyl-3-indolyl)-6-benzoxazolyl)acetic acidYield 87%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To methyl (2-(6-fluoro-1-methyl-3-indolyl)-6-benzoxazolyl)acetate (889 mg, 2.63 mmol) were added THF (25 ml) and 0.25N NaOH (15.8 ml, 3.95 mmol). The resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was poured in 1N HCl (30 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water, and dried under reduced pressure to give (2-(6-fluoro-1-methyl-3-indolyl)-6-benzoxazolyl)acetic acid (741 mg, 87%) as a brown solid.

Workup

  1. customThe crystals thus precipitated
  2. filtrationwere collected by filtration under reduced pressure
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-f1374e9da17e4d1cbbed35e7b65b7831
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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