2-Isoxazoline-3-carboxylic acid, 5-phenyl-, ethyl ester → 5-Phenyl-4,5-dihydro-1,2-oxazole-3-carboxylic acid

HRID 1918523Notes

Reaction equation

HRID 1918523 reaction equation
[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]([O:14]CC)=[O:13])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[OH-].[Na+].O1CCOCC1>[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]([OH:14])=[O:13])[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 5388222-Isoxazoline-3-carboxylic acid, 5-phenyl-, ethyl ester

Product 1

HCID 130815325-Phenyl-4,5-dihydro-1,2-oxazole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate (0.1 g; 0.4 mmol) was dissolved in a mixture of sodium hydroxide (5 mL, 1M, water) and dioxane (2 mL). The reaction mixture was stirred vigorously at room temperature overnight and concentrated under reduced pressure. The resulting solution was acidified and extracted with ethyl acetate, dried and concentrated under reduced pressure, the crude material was used without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customthe crude material was used without further purification

Sources & evidence

ORD record
ord-61b131ed624e44aab897fb59c437a4bf
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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