Methanol → 5-Chloro-2-phenyl-oxazole-4-carboxylic acid

HRID 2236174Notes

Reaction equation

HRID 2236174 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:9][C:10]=1[Cl:11])=[O:5])C.O1CCCC1.CO.[H-].[OH-].[Li+]>O>[Cl:11][C:10]1[O:9][C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:7][C:6]=1[C:4]([OH:5])=[O:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 67537623Ethyl 5-chloro-2-phenyloxazole-4-carboxylateHCID 86597229HCID 86597229, compound

Product 1

HCID 593012785-Chloro-2-phenyl-oxazole-4-carboxylic acidYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Solution of 5-chloro-2-phenyl-oxazole-4-carboxylic acid ethyl ester (92 mg, 0.37 mmol) in a mixture solution of tetrahydrofuran, methanol and water (3:1:1, 5 mL) was treated with lithium hydroxide monohydride (44 mg, 1.1 mmol) at room temperature for two hours. After the reaction was complete, solvent was evaporated. To the residue, water was added, and pH value of the aqueous layer was adjusted to ˜1-2 by addition of dilute hydrochloride acid (1N). The white precipitation was collected by centrifugation to give 5-chloro-2-phenyl-oxazole-4-carboxylic acid (73 mg, 88%). LCMS calcd for C10H6ClNO3 (m/e) 223, obsd 224 (M+H).

Workup

  1. customsolvent was evaporated
  2. additionTo the residue, water was added
  3. additionpH value of the aqueous layer was adjusted to ˜1-2 by addition of dilute hydrochloride acid (1N)
  4. customThe white precipitation
  5. customwas collected by centrifugation

Sources & evidence

ORD record
ord-57305864de79446c80ea34b5949efd85
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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