Triethylamine → Ethyl 5-chloromethylisoxazole-3-carboxylate

HRID 1952845Notes

Reaction equation

HRID 1952845 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

Conditions

Temperature
12.5 °C

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-b19144cb93244b68871c4c630c3e7db8
Source dataset
uspto-grants-2000_09
Patent number
US06114358

Reaction notes

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