Ethyl 4H-thieno[2,3-d]pyrrole-5-carboxylate Chemical Properties

Melting point:

131-132°C

Boiling point:

345.7±22.0 °C(Predicted)

Density 

1.339±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

14.65±0.30(Predicted)

Appearance

Light brown to brown Solid

InChI

InChI=1S/C9H9NO2S/c1-2-12-9(11)7-5-8-6(10-7)3-4-13-8/h3-5,10H,2H2,1H3

InChIKey

BLUDZFMRKHHPGZ-UHFFFAOYSA-N

SMILES

N1C(C(OCC)=O)=CC2SC=CC1=2

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2934999090

Ethyl 4H-thieno[2,3-d]pyrrole-5-carboxylate Usage And Synthesis

Synthesis

GENERAL METHOD: Sodium ethoxide (8.17 g, 120 mmol, 20 wt% ethanol solution) was slowly added dropwise to an anhydrous ethanol (50 mL) mixture of 2-thiophenecarboxaldehyde (2.8 mL, 30 mmol) and ethyl azidoacetate (15.4 g, 120 mmol) at -10 °C. After dropwise addition, the reaction mixture was stirred at room temperature for 4 hours. Subsequently, the reaction was quenched by addition of excess saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate (2 x 80 mL), and the organic layers were combined, washed with saturated saline (2 x 60 mL) and dried over anhydrous sodium sulfate. After removing the solvent by evaporation under reduced pressure, the residue was dissolved in toluene (30 mL) and heated to reflux for 1 hour. After completion of the reaction, it was cooled to room temperature and the solvent was removed by evaporation. The residue was purified by column chromatography (eluent: n-hexane/dichloromethane=2:1) to afford ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate (4a) as a white solid (2.93 g, 50% yield). The product was characterized by 1H NMR (400 MHz, CDCl3) and 13C NMR (100 MHz, CDCl3) with the following data: 1H NMR δ 9.26 (br s, 1H), 7.32 (d, J = 5.2 Hz, 1H), 7.14 (d, J = 0.8 Hz, 1H), 6.96 (dd, J = 5.2, 0.8 Hz, 1H ), 4.38 (q, J = 7.6 Hz, 2H), 1.39 (t, J = 7.6 Hz, 3H); 13C NMR δ 161.7, 141.3, 129.4, 127.1, 124.8, 111.1, 107.5, 60.7, 14.5.

References

[1] Tetrahedron, 2012, vol. 68, # 47, p. 9795 - 9801,7
[2] Patent: US2004/48878, 2004, A1. Location in patent: Page/Page column 10-11

Ethyl 4H-thieno[2,3-d]pyrrole-5-carboxylate(46193-76-4)Related Product Information

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