Styrene → 2-Methyl-5-phenylisoxazolidine

HRID 610625Notes

Reaction equation

HRID 610625 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:9][N+:10]([O-:12])=[CH2:11]>>[CH3:9][N:10]1[CH2:11][CH2:1][CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[O:12]1

Participants

3

Reactant 2

HCID 7501StyreneHCID 11137081Methanamine, N-methylene-, N-oxide

Product 1

HCID 110519812-Methyl-5-phenylisoxazolidine

Procedure

A mixture of styrene (37.0 g, 356 mmol) and the N-methylnitrone solution from Example 5 is heated at 85° C. for 4 hours. After cooling, the phases were separated and the aqueous phase is extracted with chloroform (2×50 g). The combined chloroform extracts were combined with the initial organic phase, and the resultant mixture is washed with water (50 g). The organic phase is dried (K2CO3) and stripped of chloroform and excess styrene to give 2-methyl-5-phenylisoxazolidine (ca. 16 g).

Workup

  1. temperatureAfter cooling
  2. customthe phases were separated
  3. extractionthe aqueous phase is extracted with chloroform (2×50 g)
  4. washthe resultant mixture is washed with water (50 g)
  5. dry with materialThe organic phase is dried (K2CO3)

Sources & evidence

ORD record
ord-315797db5b324e259f409f6fb369be40
Source dataset
uspto-grants-1999_12
Patent number
US05998627

Reaction notes

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