Water → 5-(3-Oxo-1-phenylbutyl)-4-phenyl-2-oxo-4-oxazoline

HRID 47922

Reaction equation

HRID 47922 reaction equation
[C:1]1([C:7]2[NH:8][C:9](=[O:12])[O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13](=[CH:20][C:21](=[O:23])[CH3:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CS(O)(=O)=O.O>C(#N)C.C(OCC)(=O)C>[O:23]=[C:21]([CH3:22])[CH2:20][CH:13]([C:11]1[O:10][C:9](=[O:12])[NH:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 159094-Phenyl-3-Buten-2-oneHCID 1186694-Oxazolin-2-one, 4-phenyl-

Product 1

HCID 155417565-(3-Oxo-1-phenylbutyl)-4-phenyl-2-oxo-4-oxazolineYield 86.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Phenyl-2-oxo-4-oxazoline (1.61 g) and benzalacetone (1.46 g) were dissolved in acetonitrile (20 mL), and methanesulfonic acid (0.96 mL) was added. The obtained mixture was stirred at room temperature for 1 h and water (100 mL) and ethyl acetate (100 mL) were added to the reaction mixture. The organic layer was separated, washed twice with water (50 mL), and concentrated under reduced pressure to give an oily substance. The obtained oily substance was subjected to silica gel column chromatography and eluted with n-hexane-ethyl acetate (1:1). The solvent was evaporated and isopropyl ether (50 mL) was added to the obtained oily substance to allow crystallization and the mixture was stirred at room temperature for 1 h. The crystals were collected by filtration and washed with isopropyl ether (20 mL) to give the title compound (2.65 g; yield 86.3%) as white crystals.

Workup

  1. customThe organic layer was separated
  2. washwashed twice with water (50 mL)
  3. concentrationconcentrated under reduced pressure
  4. customto give an oily substance
  5. washeluted with n-hexane-ethyl acetate (1:1)
  6. customThe solvent was evaporated
  7. additionisopropyl ether (50 mL) was added to the obtained oily substance
  8. customcrystallization
  9. stirringthe mixture was stirred at room temperature for 1 h
  10. filtrationThe crystals were collected by filtration
  11. washwashed with isopropyl ether (20 mL)

Sources & evidence

ORD record
ord-5040fe76ccd14a1ba39324277a555368
Source dataset
uspto-grants-2004_03
Patent number
US06699995B1

Linked notes

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