Ethyl Acetate → 3-(2-Oxo-1,3-oxazolidin-3-yl)benzaldehyde

HRID 38306

Reaction equation

HRID 38306 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13])=[O:7])(C)(C)[CH3:2].[H-].[Na+].BrCCO.C(OCC)(=O)C>CN(C)C=O>[O:7]=[C:6]1[N:8]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=[O:13])[CH2:2][CH2:1][O:5]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 108982-BromoethanolHCID 24758Sodium hydrideHCID 167407363-(BOC-Amino)benzaldehyde

Product 1

HCID 231318243-(2-Oxo-1,3-oxazolidin-3-yl)benzaldehydeYield 29.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2.93 g of 3-[N-(t-butoxycarbonyl)amino]benzaldehyde in 20 ml of dimethylformamide was added 0.58 g of sodium hydride (60% oily) under ice-cooling. After stirring at room temperature for 1 hour, a solution of 0.93 ml of 2-bromoethanol in 5 ml of dimethylformamide was added dropwise under ice-cooling. After stirring at room temperature for 14 hours, the mixture was heated to stir at 115° C. for 6 hours. Ethyl acetate was added, and this was washed successively with water and an aqueous saturated sedum chloride solution, dried with anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.75 g of oily 3-(2-oxo-oxazolidin-3-yl)benzaldehyde.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringAfter stirring at room temperature for 14 hours
  4. temperaturethe mixture was heated
  5. stirringto stir at 115° C. for 6 hours
  6. washthis was washed successively with water
  7. dry with materialan aqueous saturated sedum chloride solution, dried with anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-66c3dc5457934a1f8fca48a64bde6623
Source dataset
uspto-grants-2013_09
Patent number
US08524729B2

Linked notes

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