ChemicalBook CAS DataBase List 1-(3-carbethoxy-5-isoxazolyl)ethanol

1-(3-carbethoxy-5-isoxazolyl)ethanol synthesis

4synthesis methods

Product Name:1-(3-carbethoxy-5-isoxazolyl)ethanol
CAS Number:78934-71-1
Molecular formula:C8H11NO4
Molecular Weight:185.18

95080-93-6 Synthesis

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

95080-93-6
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Yield:78934-71-1 35%

Reaction Conditions:

with triethylamine in N,N-dimethyl-formamide at 90; for 17 h;Inert atmosphere;

Steps:

26.1 Step 1:

Step 1:
Preparation of ethyl 5-(1-hydroxyethyl)isoxazole-3-carboxylate
To a solution of but-3-yn-2-ol (5.0 g, 71.4 mmol) in N,N-dimethylformamide (50 mL) was added a solution of (Z)-ethyl 2-chloro-2-(hydroxyimino)acetate (4.33 g, 28.6 mmol) in N,N-dimethylformamide (10 mL) dropwise over 40 min under nitrogen.
After addition, the reaction mixture was heated to 90° C. and a solution of triethylamine (8.7 g, 85.7 mmol) in N,N-dimethylformamide (10 mL) was added dropwise over 1 h.
The reaction mixture was heated at 90° C. for 17 h, then cooled to room temperature.
The reaction mixture was diluted with ethyl acetate (150 mL), washed with water (100 mL*2) and brine (100 mL*2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo.
The residue was purified by column chromatography (silica, petroleum ether/ethyl acetate=4/1) to give ethyl 5-(1-hydroxyethyl)isoxazole-3-carboxylate (1.86 g, 10.1 mmol, 35%) as a yellow oil. LCMS (ESI) m/z: 186.1 [M+H]⁺.

References:

US2019/330198,2019,A1 Location in patent:Paragraph 0710

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861135-87-7 Synthesis