Sodium hydride → 3-(2-Bromopropionoyl)-4,4-dimethyl-1,3-oxazolan-2-one

HRID 484384Notes

Reaction equation

HRID 484384 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:10])[CH2:8][O:7][C:6](=[O:9])[NH:5]1.[Br:11][CH:12]([CH3:16])[C:13](Br)=[O:14].P([O-])(O)(O)=O.[K+]>O1CCCC1>[Br:11][CH:12]([CH3:16])[C:13]([N:5]1[C:4]([CH3:10])([CH3:3])[CH2:8][O:7][C:6]1=[O:9])=[O:14]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 79047Propanoyl bromide, 2-bromo-HCID 1413154,4-Dimethyl-1,3-oxazolidin-2-oneHCID 516951Monobasic potassium phosphate

Product 1

HCID 98563143-(2-Bromopropionoyl)-4,4-dimethyl-1,3-oxazolan-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (0.24 g; 10.0 mmol) in tetrahydrofuran (100 ml) was added 4,4-dimethyloxazolidin-2-one (1.15 g; 10.0 mmol) at 0° C., and the resultant suspension was stirred at room temperature for 5 hours. To the gelatinous reaction mixture was added 2-bromopropionyl bromide (1.05 ml) at 0° C. After stirring for 1 hour, a saturated aqueous solution of potassium dihydrogen phosphate was added to quench the reaction. An aqueous layer was extracted with ethyl acetate. Combined organic layers were dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give a solid residue, which was purified by silica gel column chromatography (hexane:dichloromethane=1:1~0:1) to give 3-(2'-bromopropionyl)-4,4-dimethyloxazolidin-2-one (2.35 g, yield, 90%) as colorless crystals.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionAn aqueous layer was extracted with ethyl acetate
  4. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto give a solid residue, which
  7. customwas purified by silica gel column chromatography (hexane:dichloromethane=1:1~0:1)

Sources & evidence

ORD record
ord-55f7d4ba2de248539b504c1da744c3c5
Source dataset
uspto-grants-1993_07
Patent number
US05231179

Reaction notes

Loading…