Sodium Hydroxide → 5-(3-Fluoro-phenyl)-2-methyl-oxazole-4-carboxylic acid

HRID 560269Notes

Reaction equation

HRID 560269 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH3:18])[O:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1)=[O:5])C.[OH-].[Na+]>CCO>[F:17][C:13]1[CH:12]=[C:11]([C:10]2[O:9][C:8]([CH3:18])=[N:7][C:6]=2[C:4]([OH:5])=[O:3])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66998781HCID 66998781, compound

Product 1

HCID 669289685-(3-Fluoro-phenyl)-2-methyl-oxazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(3-fluoro-phenyl)-2-methyl-oxazole-4-carboxylic acid ethyl ester (0.56 mmol), EtOH (0.63 mL) and aq. NaOH solution (2.0 M, 0.63 mL) is stirred for 2 h at RT and washed once with ether. The aq. layer is made acidic by addition of conc HCl and extracted twice with ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo to give the desired acid as a pure yellow solid. LC-MS (basic): tR=0.49 min; [M−H]−=220.3.

Workup

  1. washwashed once with ether
  2. additionThe aq. layer is made acidic by addition of conc HCl
  3. extractionextracted twice with ether
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-024efdc74db34ce68da23a0c591e6320
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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