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ChemicalBook CAS DataBase List 5-CYCLOPROPYLISOXAZOLE-3-CARBOXYLIC ACI&
110256-15-0

5-CYCLOPROPYLISOXAZOLE-3-CARBOXYLIC ACI& synthesis

5synthesis methods
Ethyl 5-Cyclopropylisoxazole-3-carboxylate

21080-81-9

5-CYCLOPROPYLISOXAZOLE-3-CARBOXYLIC ACI&

110256-15-0

The general procedure for the synthesis of 5-cyclopropylisoxazole-3-carboxylic acid from ethyl 5-cyclopropylisoxazole-3-carboxylate was as follows:Intermediate 16 - Preparation of 5-cyclopropylisoxazole-3-carboxylic acid. A mixture of ethyl 5-cyclopropylisoxazole-3-carboxylate (0.550 g, 3.04 mmol) with 1M aqueous sodium hydroxide (9.11 mL, 9.11 mmol) was stirred at room temperature for 72 hours. Upon completion of the reaction, the pH of the reaction solution was adjusted to 1 with 6N hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was separated, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give 0.446 g of 5-cyclopropylisoxazole-3-carboxylic acid as a solid in 96% yield. The product was confirmed by mass spectrometry: ESI/APCI(+) m/z: 154 (M+H), 176 (M+Na); ESI/APCI(-) m/z: 152 (M-H).

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Yield:-

Steps:

Multi-step reaction with 2 steps
1.1: 1,4-diaza-bicyclo[2.2.2]octane / ethanol / 0.33 h / 150 °C / Microwave irradiation
2.1: water; sodium hydroxide / 72 h / 20 °C
2.2: pH 1

References:

KATHOLIEKE UNIVERSITEIT LEUVEN, K.U. LEUVEN R&;D;reMYND;GRIFFIOEN, Gerard;VAN DOOREN, Tom;ROJAS DE LA PARRA, Veronica;MARCHAND, Arnaud;ALLASIA, Sara;KILONDA, Amuri;CHALTIN, Patrick WO2010/142801, 2010, A1

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