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

HRID 47921

Reaction equation

HRID 47921 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:1]1([C:7]2[NH:8][C:9](=[O:12])[O:10][C:11]=2[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:20][C:21](=[O:23])[CH3:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

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 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-phenyl-2-oxo-4-oxazoline (1.61 g) and benzalacetone (1.46 g) in acetonitrile (20 ml) was added dropwise methanesulfonic acid (0.96 g). After stirring the obtained mixture at room temperature for 30 min, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried (MgSO4), and the solvent was evaporated. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (1:1). The solvent was evaporated. Crystallization from isopropyl ether gave 4-(4-phenyl-2-oxo-4-oxazolin-5-yl)-4-phenyl-2-butanone (2.65 g; yield 86.3%). Recrystallization from ethanol gave colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated
  5. washeluted with hexane-ethyl acetate (1:1)
  6. customThe solvent was evaporated
  7. customCrystallization from isopropyl ether

Sources & evidence

ORD record
ord-547f94840dbf42e1b5c1663b995de3f7
Source dataset
uspto-grants-2004_03
Patent number
US06699995B1

Linked notes

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