2,3-DIHYDRO-4-BENZOFURANCARBOXALDEHYDE Chemical Properties

Boiling point:

276℃

Density 

1.222

Flash point:

132℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Light yellow to yellow Solid

2,3-DIHYDRO-4-BENZOFURANCARBOXALDEHYDE Usage And Synthesis

Uses

2,3-Dihydrobenzofuran-4-carbaldehyde is used in the synthesis of macroline derivatives as inhibitors of mycobacterium tuberculosis protein tyrosine phosphatase B.

Synthesis

The general procedure for the synthesis of 2,3-dihydrobenzofuran-4-carbaldehyde from 4-hydroxymethyl-benzodihydrofuran was as follows: a dichloromethane solution (40 mL, 2 M) of oxalyl chloride was stirred at -78 °C and DMSO (8.10 mL, 114 mmol) was slowly added. Subsequently, a dichloromethane solution (35 mL) of 4-hydroxymethyl-benzodihydrofuran (8.53 g, 56.9 mmol) was added dropwise and stirring was continued for 30 min at -78 °C. Upon completion of the reaction, triethylamine (33 mL, 228 mmol) was carefully added to quench the reaction. The resulting suspension was stirred at room temperature for 30 min and then diluted with dichloromethane (100 mL). The organic layer was washed three times with water and twice with brine sequentially, and finally concentrated by vacuum to give 2,3-dihydrobenzofuran-4-carbaldehyde as an oil (8.42 g, 100%), which could be used for subsequent reactions without further purification.

References

[1] Patent: EP1041980, 2005, B1. Location in patent: Page 17
[2] Patent: EP1027043, 2004, B1. Location in patent: Page/Page column 17

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