ETHYL 5-TERT-BUTYLISOXAZOLE-3-CARBOXYLATE Chemical Properties

Boiling point:

108-111 °C(Press: 5.5 Torr)

Density 

1.057±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-4.93±0.50(Predicted)

Appearance

Colorless to light yellow Liquid

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2934999090

ETHYL 5-TERT-BUTYLISOXAZOLE-3-CARBOXYLATE Usage And Synthesis

Synthesis

General procedure for the synthesis of ethyl 5-tert-butyl-isoxazole-3-carboxylate from the compound (CAS:94122-76-6): tert-butyl alkenone (50) (6.00 g, 30.0 mmol) was dissolved in anhydrous ethanol/THF (1:1, 70 mL) and stirred at room temperature. To this solution was added hydroxylamine hydrochloride (2.29 g, 33.0 mmol) and the resulting mixture was stirred under nitrogen protection for 12 hours. Subsequently, the mixture was transferred to a Soxhlet extractor fitted with molecular sieves and heated to reflux for 2 hours. After completion of the reaction, the mixture was allowed to cool and the solvent was removed by evaporation. Water (100 mL) was added and the mixture was extracted with dichloromethane (2 x 100 mL). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography to afford ethyl 5-tert-butyl-isoxazole-3-carboxylate (54) as a colorless oil (3 g, 51% yield).1H NMR (500 MHz, CDCl3) data for 54: δ 6.37 (s, 1H), 4.43 (q, 2H), 1.41 (t, 3H), 1.37 (s, 9H).

References

[1] Patent: US2006/199853, 2006, A1. Location in patent: Page/Page column 45
[2] Patent: US2006/223884, 2006, A1. Location in patent: Page/Page column 57-58

ETHYL 5-TERT-BUTYLISOXAZOLE-3-CARBOXYLATE(91252-54-9)Related Product Information

• 5-TERT-BUTYL-ISOXAZOLE-3-CARBOXYLIC ACID METHYL ESTER
• 3-Isoxazolecarboxylicacid,5-(1,1-dimethylethyl)-(9CI)
• Methyl 5-methylisoxazole-3-carboxylate
• 3,5-Dimethylisoxazole
• 5-Isopropylisoxazole-3-carboxylic acid
• 5-Methylisoxazole-3-carboxaldehyde
• 5-Methylisoxazole-3-carboxylic acid
• 3-Isoxazolemethanol
• 3-Isoxazolecarboxylic acid
• Isoxazole-3-carbaldehyde
• (5-Methylisoxazol-3-yl)methanol
• ETHYL 5-METHYLISOXAZOLE-3-CARBOXYLATE
• AKOS PAO-1432
• 3-Isoxazolecarboxylic acid, methyl ester (8CI,9CI)
• 3-Isoxazolecarboxylicacid,5-ethyl-,ethylester(7CI,9CI)
• ETHYL ISOXAZOLE-3-CARBOXYLATE
• 5-ETHYL-ISOXAZOLE-3-CARBOXYLIC ACID
• ETHYL 5-TERT-BUTYLISOXAZOLE-3-CARBOXYLATE