Acetic Acid → Ethyl 4-[4-(4-fluorophenyl)-2-oxo-4-oxazolin-5-yl]butanoate

HRID 747455Notes

Reaction equation

HRID 747455 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([O:18][C:19]([O:21]C2C=CC=CC=2)=O)[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:33].C(O)(=O)C>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:33][C:19](=[O:21])[O:18][C:9]=2[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 18174739Ethyl 6-(4-fluorophenyl)-6-oxo-5-phenoxycarbonyloxyhexanoate

Product 1

HCID 18174763Ethyl 4-[4-(4-fluorophenyl)-2-oxo-4-oxazolin-5-yl]butanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 6-(4-fluorophenyl)-6-oxo-5-phenoxycarbonyloxyhexanoate (18.0 g), ammonium acetate (17.8 g) and acetic acid (100 ml) was stirred with heating under reflux for 2 hours. The reaction mixture was poured into water (500 ml) and extracted with ethyl acetate (200 ml×2), and the extract was washed with water (200 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 4-[4-(4-fluorophenyl)-2-oxo-4-oxazolin-5-yl]butanoate was obtained as an oil (7.67 g, 56%) from an ethyl acetate-hexane (1:1, v/v)-eluted fraction.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate (200 ml×2)
  4. washthe extract was washed with water (200 ml)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-41782bc7d0514927bfa3af2be7765366
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Reaction notes

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