Triethylamine → Ethyl 5-chloromethylisoxazole-3-carboxylate

HRID 1582902Notes

Reaction equation

HRID 1582902 reaction equation
C(N(CC)CC)C.Cl[C:9](=[N:15][OH:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH2:17]([Cl:20])[C:18]#[CH:19]>O>[Cl:20][CH2:17][C:18]1[O:16][N:15]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122213-Chloro-1-propyneHCID 6816376Ethyl chloro(hydroximino)acetate

Product 1

HCID 14674306Ethyl 5-chloromethylisoxazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

21.2 g (210 mmol) of triethylamine were added dropwise with stirring to a mixture, cooled to 10-15° C., of 30 g (198 mmol) of ethyl 2-chloro-2-hydroxyiminoacetate and 150 ml of propargyl chloride, stirring was continued for 1 hour at room temperature, water was subsequently added, the mixture was extracted with ether, and the organic phase was dried over magnesium sulfate and evaporated in vacuo in a rotary evaporator. The residue was distilled in vacuo at 0.5 torr, the product distilling over at 116-122° C.

Workup

  1. stirringstirring
  2. extractionthe mixture was extracted with ether
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. customevaporated in vacuo in a rotary evaporator
  5. distillationThe residue was distilled in vacuo at 0.5 torr
  6. distillationthe product distilling over at 116-122° C.

Sources & evidence

ORD record
ord-9ecd1bedd4c042fa8e17bc3f8c81beb5
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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