Tetrahydrofuran → HCID 68884593, compound

HRID 1294291Notes

Reaction equation

HRID 1294291 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[N:20]=[C:19]([CH2:21][O:22][C:23]2[CH:24]=[C:25]([CH2:29][C:30]([O:32]C)=[O:31])[CH:26]=[CH:27][CH:28]=2)[CH:18]=[CH:17][CH:16]=1.O1CCCC1.[OH-].[Na+]>CO>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[N:20]=[C:19]([CH2:21][O:22][C:23]2[CH:24]=[C:25]([CH2:29][C:30]([OH:32])=[O:31])[CH:26]=[CH:27][CH:28]=2)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68885468HCID 68885468, compound

Product 1

HCID 68884593HCID 68884593, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl 2-[3-[[6-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-2-pyridyl]methoxy]phenyl]acetate (1.10 g), tetrahydrofuran (5 mL) and methanol (5 mL) was added a 1N aqueous sodium hydroxide solution (5.0 mL) and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was concentrated, and water and dilute hydrochloric acid were added to acidify the residue. The precipitated solid was collected by filtration and dried with air to give crystals (0.85 g, 80%) of 2-[3-[[6-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-2-pyridyl]methoxy]phenyl]acetic acid. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 97-98° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater and dilute hydrochloric acid were added
  3. filtrationThe precipitated solid was collected by filtration
  4. customdried with air

Sources & evidence

ORD record
ord-df4dfbdcfa7045afb082a6db93474ada
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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