1,4-Dioxane → Ethyl 5-(2-(trifluoromethyl)phenyl)isoxazole-4-carboxylate

HRID 1389014Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:22])[C:5]([C:10](=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([F:20])([F:19])[F:18])=[CH:6][N:7](C)C)[CH3:2].O1CCOCC1.Cl.NO>O>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[N:7][O:21][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([F:20])([F:19])[F:18])=[O:22])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

Ethyl-2-(2'-trifluoromethylbenzoyl)-3-dimethylaminopropenoate (3.14 g.; 0.01 mol.) was dissolved in 15 ml. of dioxane. To this solution was added a solution of hydroxylamine hydrochloride (1.05 g.; 0.015 mol.) in 5 ml. of water. The resulting solution was stirred for 14 hours at 25° C. Extraction with water and diethyl ether yielded ethyl-5-(2'-trifluoromethylphenyl)-4-isoxazolecarboxylate as an oil (1.6 g.; 56.2% yield) having the following analysis:

Workup

extractionExtraction with water and diethyl ether

Sources & evidence

ORD record: ord-ffce516bdfa54b64a150943b113198d7
Source dataset: uspto-grants-1981_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04243406

Reaction notes

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