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

HRID 58536

Reaction equation

HRID 58536 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-ab4ec2da78fa428b9c4bb3e01e132049
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

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