ChemicalBook CAS DataBase List ETHYL 5-TERT-BUTYLISOXAZOLE-3-CARBOXYLATE

ETHYL 5-TERT-BUTYLISOXAZOLE-3-CARBOXYLATE synthesis

6synthesis methods

Product Name:ETHYL 5-TERT-BUTYLISOXAZOLE-3-CARBOXYLATE
CAS Number:91252-54-9
Molecular formula:C10H15NO3
Molecular Weight:197.23

13395-36-3
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$13.43/250mgs:

ETHYL 5-TERT-BUTYLISOXAZOLE-3-CARBOXYLATE

91252-54-9
79 suppliers
$55.00/250 mg

Yield: 65%

Reaction Conditions:

with hydroxylamine hydrochloride;sodium hydrogencarbonate in ethanol for 16 h;Reflux;

Steps:

B.1
The title compound is prepared by those skilled in the art according to a literature procedure (Lepage et al, Eur. J. Med. Chem., 1992, 27, 6, 581-93).To a solution of sodium hydrogen carbonate (2.10 g, 25 mmol) and hydroxylamine hydrochloride (1.73 g, 25 mmol) in ethanol (25 mL) is added ethyl trimethyl acetopyruvate (5.00 g, 25 mmol). The mixture is heated at reflux for 16 h. After this time the sodium chloride is removed by filtration and the filtrate is concentrated under reduced pressure. The residue is purified by chromatography on silica eluting with 8/2 cyclohexane/ethyl acetate to provide the title compound as a yellow oil (3.2 g, 65%), m/z 198 [M+H⁺]. ¹H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.38 (9 H, s), 1.42 (3 H, t, /=7.15 Hz), 4.44 (2 H, q, /=7.15 Hz), 6.38 (1 H, s).

References:

BOEHRINGER INGELHEIM INTERNATIONAL GMBH;BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG WO2009/140089, 2009, A2 Location in patent:Page/Page column 37