Chloroform → 2-Chloro-1-(isoxazolidin-2-yl)propan-1-one

HRID 543575Notes

Reaction equation

HRID 543575 reaction equation
Cl.[O:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.C(Cl)(Cl)Cl.[Cl:11][CH:12]([CH3:16])[C:13](Cl)=[O:14].C(N(CC)CC)C>O>[Cl:11][CH:12]([CH3:16])[C:13]([N:3]1[CH2:4][CH2:5][CH2:6][O:2]1)=[O:14]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 1110192-Chloropropionyl chlorideHCID 12304500Isoxazolidine hydrochloride

Product 1

HCID 133146162-Chloro-1-(isoxazolidin-2-yl)propan-1-oneYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of isoxazolidine hydrochloride (11.0 g) and chloroform (200 ml) was added (±)-2-chloropropionyl chloride (13.3 g) under ice-cooling and stirring and then added dropwise triethylamine (22.2 g) under the same conditions. The stirring was continued at room temperature for further one hour, after which an amount of water was added to the reaction mixture to form layers. The organic layer thus separated was washed with 1 N hydrochloric acid and then with a 5% aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate. Removal of the solvent by a distillation in vacuo gave N-[(±)-2-chloropropionyl]isoxazolidine (15.0 g) as a pale yellow oil. Purification of the oil by silica gel column chromatography afforded a colorless oil. nD20 =1.4918.

Workup

  1. temperaturecooling
  2. customto form layers
  3. customThe organic layer thus separated
  4. washwas washed with 1 N hydrochloric acid
  5. dry with materialwith a 5% aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate
  6. customRemoval of the solvent
  7. distillationby a distillation in vacuo

Sources & evidence

ORD record
ord-a2395f5bbfa940c9a5a470319191bb8c
Source dataset
uspto-grants-1984_05
Patent number
US04447259

Reaction notes

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