Water → Benzyl (3-oxomorpholin-4-yl)acetate

HRID 2068869Notes

Reaction equation

HRID 2068869 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:7].[H-].[Na+].Br[CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].O>CN(C)C=O.C(OCC)(=O)C>[O:7]=[C:2]1[CH2:3][O:4][CH2:5][CH2:6][N:1]1[CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 62576Benzyl bromoacetateHCID 669533-Morpholinone

Product 1

HCID 58550356Benzyl (3-oxomorpholin-4-yl)acetateYield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an argon atmosphere, to a solution of morpholin-3-one (220 mg, 2.2 mmol) in N,N-dimethylformamide (2.2 ml) was added sodium hydride (105 mg, 2.6 mmol) under ice-cooling, and the mixture was stirred for 1 hr. Then, benzyl bromoacetate (379 μl, 2.4 mmol) was added, and the mixture was stirred for 2 hr. To the reaction solution were added water and ethyl acetate, and the organic layer was separated. The aqueous layer was extracted twice with ethyl acetate, and the combined organic layers were washed successively with water and saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (321 mg, yield 59%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 2 hr
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. washthe combined organic layers were washed successively with water and saturated brine
  6. dry with materialdried over sodium sulfate
  7. customSodium sulfate was removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8a09a8aa6940485a950405e98f20bc0d
Source dataset
uspto-grants-2012_10
Patent number
US08299070B2

Reaction notes

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