Ethyl 2-chloro-1,3-oxazole-5-carboxylate Chemical Properties

Boiling point:

254.1±32.0 °C(Predicted)

Density 

1.332±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

-2?+-.0.10(Predicted)

form 

liquid

color 

Orange

InChI

InChI=1S/C6H6ClNO3/c1-2-10-5(9)4-3-8-6(7)11-4/h3H,2H2,1H3

InChIKey

ZFLDTEIDAGWEEI-UHFFFAOYSA-N

SMILES

O1C(C(OCC)=O)=CN=C1Cl

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant/Keep Cold

HS Code 

2934999090

Ethyl 2-chloro-1,3-oxazole-5-carboxylate Usage And Synthesis

Synthesis

General procedure for the synthesis of ethyl 2-chlorooxazole-5-carboxylate from ethyl oxazole-5-carboxylate: to a solution of ethyl oxazole-5-carboxylate (15.0 g, 106 mmol) in tetrahydrofuran (THF, 150 mL) was added slowly and dropwise to a solution of lithium hexamethyldisilanamide (LiHMDS, 178 mL, 170 mmol) at -60 °C. The reaction mixture was stirred continuously at -50 °C for 1 hour. Subsequently, hexachloroethane (37.8 g, 160 mmol) was added to the reaction system. The reaction mixture was warmed to room temperature and stirred for 12 hours. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride (NH4Cl) solution (50 mL) and subsequently extracted with ethyl acetate (EtOAc, 50 mL). The organic layer was separated, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography to afford the target product ethyl 2-chlorooxazole-5-carboxylate (10 g, 56% yield) as a colorless oil.1H NMR (400 MHz, CDCl3) δ 7.71 (s, 1H), 3.39 (q, J=7.2 Hz, 2H), 1.38 (t, J=7.2 Hz, 3H).

References

[1] Organic Letters, 2005, vol. 7, # 15, p. 3351 - 3354
[2] Patent: WO2015/116663, 2015, A1. Location in patent: Paragraph 0116

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