ChemicalBook CAS DataBase List ETHYL 5-(HYDROXYMETHYL)ISOXAZOLE-3-CARBOXYLATE

ETHYL 5-(HYDROXYMETHYL)ISOXAZOLE-3-CARBOXYLATE synthesis

5synthesis methods

Product Name:ETHYL 5-(HYDROXYMETHYL)ISOXAZOLE-3-CARBOXYLATE
CAS Number:123770-62-7
Molecular formula:C7H9NO4
Molecular Weight:171.15

95080-93-6 Synthesis

(Z)-Ethyl 2-chloro-2-(hydroxyiMino)acetate

95080-93-6
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ETHYL 5-(HYDROXYMETHYL)ISOXAZOLE-3-CARBOXYLATE

123770-62-7
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Yield: 81%

Reaction Conditions:

with triethylamine in tetrahydrofuran at 0 - 25;

Steps:

ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate
In a 100 mL round-bottomed flask (Z)-ethyl 2-chloro-2-(hydroxyimino)acetate (164.96 mmol) and propargyl alcohol (824.82 mmol) were taken in tetrahydrofuran (200 mL) to give a yellow solution. Reaction mass was cooled to 0 °C and triethyl amine (197.96 mmol) in tetrahydrofuran (100 mL) was added slowly over 45 min. Reaction mass was then allowed to cool to 25 °C and stirred overnight. The reaction mass was diluted with brine (250 mL) and extracted with dichloromethane (3x 300 mL). Dichloromethane layers were collected and dried over sodium sulphate and concentrated to give crude mass which on purification over combiflash gave ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate (81 %) as pure liquid. 1H MR (300 MHz, DMSO-i) δ ppm 3.82 (t, J=7.06 Hz, 3 H) 6.74 - 6.98 (m, 2 H) 7.08 - 7.18 (m, 2 H) 8.25 - 8.39 (m, 1 H) 9.25 (s, 1 H) MS (ES⁺), (M+H)⁺ = 172.26 for C₉H₉N0₄

References:

FOUNDATION FOR NEGLECTED DISEASE RESEARCH;RATAN KALE, Ramesh;MADHAVAPEDDI, Prashanti;RAGHUNATH GHORPADE, Sandeep;VITHALRAO BELLALE, Eknath;GANPAT KALE, Manoj;RAICHURKAR, Anandkumar;LANDGE, Sudhir;DOUGLAS COWEN, Scott;ANTHONY READ, Jonathan;IYER, Pravin;NARAYANAN, Shridhar WO2015/181799, 2015, A1 Location in patent:Page/Page column 16; 17

626-35-7 Synthesis