Ethyl Acetate → 4-Benzyl-2-(2-methyl-1,3-dioxolan-2-yl)-5-oxomorpholine

HRID 1029664Notes

Reaction equation

HRID 1029664 reaction equation
[H-].[Na+].[CH2:3]([N:10]([CH2:15][CH:16]([C:18]1([CH3:23])[O:22][CH2:21][CH2:20][O:19]1)[OH:17])[C:11](=[O:14])[CH2:12]Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OCC)(=O)C>O1CCCC1>[CH2:3]([N:10]1[C:11](=[O:14])[CH2:12][O:17][CH:16]([C:18]2([CH3:23])[O:22][CH2:21][CH2:20][O:19]2)[CH2:15]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 151173012-[2-(N-benzyl-N-chloroacetylamino)-1-hydroxyethyl]-2-methyl-1,3-dioxolane

Product 1

HCID 151173024-Benzyl-2-(2-methyl-1,3-dioxolan-2-yl)-5-oxomorpholineYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60% in oil, 0.75 g) in tetrahydrofuran (50 ml) was added a solution of 2-[2-(N-benzyl-N-chloroacetylamino)-1-hydroxyethyl]-2-methyl-1,3-dioxolane (5.35 g) in tetrahydrofuran (15 ml) under ice-cooling. The mixture was heated under reflux for 4 hours and poured into a mixture of ice-water (100 ml) and ethyl acetate (150 ml). The organic layer was separated, dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (50 g) and eluted with a mixture of hexane and ethyl acetate (7:3, V/V) to give 4-benzyl-2-(2-methyl-1,3-dioxolan-2-yl)-5-oxomorpholine (4.65 g) as a syrup.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 4 hours
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a syrup
  8. washeluted with a mixture of hexane and ethyl acetate (7:3, V/V)

Sources & evidence

ORD record
ord-b424cfbc27fd44df95866b01cb741163
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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