2-Thiophenecarboxaldehyde → Thiophene, 2-(2-phenylethenyl)-

Temperature

-78 °C

Benzyldiethylphosphonate (5.7 g, 25 mmol) was dissolved in THF (50 mL) and cooled to -78° C. and nBuLi (2.5 M in hexane, 25 mmol) was added dropwise and the mixture was stirred for 30 min. Then a solution of thiophene-2-carboxaldehyde (2.8 g, 25 mmol) in THF (10 mL) was added dropwise at -78° C. The cold bath was removed and the reaction was warmed to room temperature, heated for 2 h at reflux and the reaction was then cooled and saturated aqueous NH4Cl was added. The mixture was diluted with water and extracted with ether. The organic extract was washed with brine, dried over MgSO4, filtered, and concentrated to provide a solid which was purified by recrystallization from hexane to give 2.6 g of intermediate.

1. customThe cold bath was removed
2. temperaturethe reaction was warmed to room temperature
3. temperatureheated for 2 h
4. temperatureat reflux
5. temperaturethe reaction was then cooled
6. additionsaturated aqueous NH4Cl was added
7. additionThe mixture was diluted with water
8. extractionextracted with ether
9. extractionThe organic extract
10. washwas washed with brine
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated
14. customto provide a solid which
15. customwas purified by recrystallization from hexane

ORD record

ord-0423dced8b9145b5868e72e2f3a01599

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05185363