Water → 3-(2-Propynyl)-4,5-diphenyl-oxazol-2-one

HRID 399192Notes

Reaction equation

HRID 399192 reaction equation
[C:1]1([C:7]2[NH:8][C:9](=[O:18])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:21](Br)[C:22]#[CH:23].O>CN(C=O)C>[CH2:23]([N:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:10][C:9]1=[O:18])[C:22]#[CH:21]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 1512454,5-Diphenyl-4-oxazolin-2-one

Product 1

HCID 189704433-(2-Propynyl)-4,5-diphenyl-oxazol-2-oneYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,5-Diphenyloxazol-2-one (500 mg, 2.11 mmol) was dissolved in DMF (4 ml) and sodium hydride (153 mg, 2.55 mmol) was added under nitrogen and with ice cooling over 20 minutes. After stirring for 20 minutes, propargyl bromide (210 μl, 2.79 mmol) was added. After stirring for 15 minutes with ice cooling and stirring at room temperature for 2 hours, water (20 ml) was added and the mixture was extracted with ethyl acetate. The extract was washed in turn with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 3-(2-propynyl)-4,5-diphenyl-oxazol-2-one.

Workup

  1. stirringAfter stirring for 15 minutes with ice cooling
  2. stirringstirring at room temperature for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed in turn with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1e055489136f4a9cb35afab3646c2498
Source dataset
uspto-grants-1998_10
Patent number
US05817826

Reaction notes

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