Potassium Hydroxide → 2-Isoxazolidinecarboxylic acid, ethyl ester

HRID 1733447Notes

Reaction equation

HRID 1733447 reaction equation
C(Br)CCBr.[C:6]([N:11]1[CH2:15][CH2:14][CH2:13][O:12]1)([O:8][CH2:9][CH3:10])=[O:7].[OH-].[K+]>>[C:6]([N:11]1[CH2:15][CH2:14][CH2:13][O:12]1)([O:8][CH2:9][CH3:10])=[O:7]

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 20299603HCID 20299603, compound

Product 1

HCID 5336912-Isoxazolidinecarboxylic acid, ethyl ester

Procedure

N-Carbethoxyisooxazolidine Trimethylene dibromide (40.4 g; 0.4 mole) and an ethanolic solution (224 ml.) containing potassium hydroxide (22.4 g.; 0.4 mole) are boiled together on a steam bath for six hours. The ethanol is removed by distillation and the residue triturated with ether (3×100 ml.). The combined ether washes are dried over anhydrous magnesium sulfate, filtered and concentrated to give a liquid which is vacuum distilled to give N-carbethoxyisooxazolidine, b.p. 103° C./13 mm.

Workup

  1. customThe ethanol is removed by distillation
  2. customthe residue triturated with ether (3×100 ml.)
  3. dry with materialThe combined ether washes are dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a liquid which
  7. distillationdistilled

Sources & evidence

ORD record
ord-86d8d24da0ef42e8bce93d446dc10c72
Source dataset
uspto-grants-1980_12
Patent number
US04242339

Reaction notes

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