Sodium Hydroxide → 2,4-Diphenyl-5-oxazolecarboxylic acid

HRID 585114Notes

Reaction equation

HRID 585114 reaction equation
C([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:5])C.[OH-].[Na+]>O1CCOCC1>[C:11]1([C:9]2[O:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:8]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9900703HCID 9900703, compound

Product 1

HCID 98784592,4-Diphenyl-5-oxazolecarboxylic acidYield 94.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the above-prepared 2,4-diphenyl-oxazole-5-carboxylic acid ethyl ester (500 mg, 1.70 mmole, 1.0 eq) in dioxane (6 ml) was treated with 2N NaOH (1.7 ml, 3.4 mmole, 2.0 eq) and the mixture stirred at room temperature overnight under nitrogen. The mixture was then partitioned between ethyl acetate and 2.0N HCl. The organic phase washed with 0.5N HCl and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give 426 mg of the title compound as a crude yellow solid. The product was used directly in the next step, without purification.

Workup

  1. customThe mixture was then partitioned between ethyl acetate and 2.0N HCl
  2. washThe organic phase washed with 0.5N HCl and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34bdd2179d134574802be73d328d468a
Source dataset
uspto-grants-2005_08
Patent number
US06930116B2

Reaction notes

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