Ethanol → 4-Ethyl-1,3-oxazole-5-carboxylic acid

HRID 639658Notes

Reaction equation

HRID 639658 reaction equation
C([O:3][C:4]([C:6]1[O:10][CH:9]=[N:8][C:7]=1[CH2:11][CH3:12])=[O:5])C.[OH-].[Na+].C(O)C>C(OCC)C>[CH2:11]([C:7]1[N:8]=[CH:9][O:10][C:6]=1[C:4]([OH:5])=[O:3])[CH3:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 19018567Ethyl 4-ethyloxazole-5-carboxylate

Product 1

HCID 534346434-Ethyl-1,3-oxazole-5-carboxylic acidYield 67.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Ethyl-oxazole-5-carboxylic acid ethyl ester (4.6 g) was stirred in a solution of 1N NaOH (25 ml) and ethanol (1 ml). The reaction mixture was then stirred at room temperature for 16 hours. Diethyl ether (25 ml) was added, and then the aqueous layer separated and acidified with 1N HCl (26 ml). A yellow solid formed that was collected by filtration, washed with water, then with n-pentane, providing the title compound (2.6 g) as a white solid.

Workup

  1. customthe aqueous layer separated
  2. customA yellow solid formed
  3. filtrationthat was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-29032b92a01c4c38b899649bffbd395f
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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