Ethyl 5-phenyl-3-isoxazolecarboxylate

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Ethyl 5-phenyl-3-isoxazolecarboxylate Basic information
Product Name:Ethyl 5-phenyl-3-isoxazolecarboxylate
Synonyms:TIMTEC-BB SBB014614;ethyl 3-phenyl-5-isoxazolecarboxylate
CAS:13599-24-1
MF:C12H11NO3
MW:217.22
EINECS:
Product Categories:
Mol File:13599-24-1.mol
Ethyl 5-phenyl-3-isoxazolecarboxylate Structure
Ethyl 5-phenyl-3-isoxazolecarboxylate Chemical Properties
Melting point 47 °C
Boiling point 379.8±30.0 °C(Predicted)
density 1.173±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka-4.43±0.50(Predicted)
AppearanceWhite to off-white Solid
Safety Information
MSDS Information
Ethyl 5-phenyl-3-isoxazolecarboxylate Usage And Synthesis
Synthesis
ALPHA-CHLOROBENZALDOXIME

81745-44-0

Ethyl propiolate

623-47-2

ETHYL 5-PHENYL-3-ISOXAZOLECARBOXYLATE

13599-24-1

General procedure for the synthesis of ethyl 3-phenylisoxazole-5-carboxylate from (E)-N-hydroxybenzimidoyl chloride and ethyl propargylate: preparation of the intermediate 54-ethyl S-phenylisoxazole-δ-carboxylic acid ethyl ester. The reaction was carried out by stirring ethyl propiolate (0.657 mL, 6.43 mmol), (E)-N-hydroxybenzenecarboximidoyl chloride (0.500 g, 3.21 mmol), and sodium bicarbonate (0.818 g, 9.64 mmol) in a mixed solvent of ethyl acetate (16 mL) and water (1 mL) at room temperature overnight. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The crude product was purified by fast column chromatography on silica gel, the eluent being a heptane solution of 5% to 80% dichloromethane, to give 0.295 g of ethyl 3-phenylisoxazole-5-carboxylate in 42% yield.ESI/APCI (+): 218 (M + H).

References[1] Patent: WO2010/142801, 2010, A1. Location in patent: Page/Page column 162-163
Ethyl 5-phenyl-3-isoxazolecarboxylate Preparation Products And Raw materials
Raw materialsBenzaldoxime-->alpha-Chlorobenzaldoxime-->Ethyl propiolate-->Sodium bicarbonate
Tag:Ethyl 5-phenyl-3-isoxazolecarboxylate(13599-24-1) Related Product Information
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