Ethanol → 2-Methyl-5-phenylisoxazolidine

HRID 610626Notes

Reaction equation

HRID 610626 reaction equation
[CH2:1]=[O:2].[CH3:3][NH2:4].[CH3:5][CH2:6]O.C=C[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.OO>>[CH3:3][N:4]1[CH2:6][CH2:5][CH:1]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:2]1

Participants

6

Reactant 5

HCID 702EthanolHCID 712FormaldehydeHCID 784Hydrogen PeroxideHCID 6329MethylamineHCID 7501Styrene

Product 1

HCID 110519812-Methyl-5-phenylisoxazolidine

Procedure

Paraformaldehyde (20.0 g, 724 mmol) was added in portions to 33% MeNH2 in EtOH (68.0 g, 724 mmol). Styrene (75.0 g, 721 mmol) and NaWO4.2H2O (3.4 g, 10 mmol) were added and the solution was heated to reflux. Fifty per cent H2O2 (50.0 g, 735 mmol) was added dropwise over 2 hours. After cooling, the phases were separated and the lower aqueous phase was extracted with ether (3×100 mL). The upper organic layer was combined with the ether extracts and washed with brine (2 x 100 mL). The ether and excess styrene were removed in vacuo to give (2-methyl-5-phenylisoxazolidine) as a brown oil (34.3 g, 29% based on MeNH2).

Workup

  1. temperaturethe solution was heated to reflux
  2. temperatureAfter cooling
  3. customthe phases were separated
  4. extractionthe lower aqueous phase was extracted with ether (3×100 mL)
  5. washwashed with brine (2 x 100 mL)
  6. customThe ether and excess styrene were removed in vacuo

Sources & evidence

ORD record
ord-b4e2c53a5b064c14bd646a21badb6a01
Source dataset
uspto-grants-1999_12
Patent number
US05998627

Reaction notes

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