Styrene → 2-Methyl-5-phenylisoxazolidine

HRID 443167Notes

Reaction equation

HRID 443167 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 are separated and the aqueous phase is extracted with chloroform (2×50 g). The combined chloroform extracts are 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 (16 g).

Workup

  1. temperatureAfter cooling
  2. customthe phases are separated
  3. extractionthe aqueous phase is extracted with chloroform (2×50 g)
  4. washthe resultant mixture is washed with water (50 g)

Sources & evidence

ORD record
ord-115501bff9bc403eb5fe4103264a41e5
Source dataset
uspto-grants-1999_04
Patent number
US05892117

Reaction notes

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