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ChemicalBook CAS DataBase List ETHYL 5-ACETYLISOXASOLE-3-CARBOXYLATE
104776-70-7

ETHYL 5-ACETYLISOXASOLE-3-CARBOXYLATE synthesis

2synthesis methods
-

Yield: 89%

Reaction Conditions:

with 2-iodoxybenzoic acid in ethyl acetate at 80; for 17 h;

Steps:

26.2 Step 2:
Step 2:
Preparation of ethyl 5-acetylisoxazole-3-carboxylate
To a solution of ethyl 5-(1-hydroxyethyl)isoxazole-3-carboxylate (5.0 g, 27.0 mmol) in ethyl acetate (50 mL) was added 2-iodoxybenzoic acid (22.7 g, 81.1 mmol).
After addition, the reaction mixture was heated to 80° C. and stirred for 17 h, then cooled to room temperature.
The reaction mixture was filtered and concentrated in vacuo.
The residue was purified by column chromatography (silica, petroleum ether/ethyl acetate=6/1) to give ethyl 5-acetylisoxazole-3-carboxylate (4.4 g, 24.0 mmol, 89%) as a yellow oil. LCMS (ESI) m/z: 184.1 [M+H]+.

References:

Yumanity Therapeutics, Inc.;WRONA, Iwona;TIVITMAHAISOON, Parcharee;TARDIFF, Daniel;PANDYA, Bhaumik;OZBOYA, Kerem;LUCAS, Matthew;BOURDONNEC, Bertrand Le US2019/330198, 2019, A1 Location in patent:Paragraph 0712

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