Furan → 2-(4-Chlorobutyl)furan

Temperature

-25 °C

Furan (1.36 g) was dissolved in tetrahydrofuran (50 ml) and cooled to -25° C. Hexane solution (12.5 ml) of n-butyllithium of 1.68 mol/l was added to the reaction solution, which was stirred at -15° C. for 4 hours. Subsequently, 1-bromo-4-chlorobutane (3.43 g) was dissolved in tetrahydrofuran (2.5 ml) and added to the reaction solution. This solution was further stirred at -15° C. for 1 hour and stood overnight at room temperature. The reaction solution was poured into icy water and extracted with ether. The extracted solution was successively washed with water, a saturated ammonium chloride solution and a saturated sodium chloride solution. It was then dried over magnesium sulfate and filtered. The filtrate was concentrated and the resultant oil-like product was purified by distillation under reduced pressure (130° C./12 mmHg). The object compound (2.87 g) was obtained in the form of oil.

1. additionadded to the reaction solution
2. stirringThis solution was further stirred at -15° C. for 1 hour
3. waitstood overnight at room temperature
4. extractionextracted with ether
5. washThe extracted solution was successively washed with water
6. dry with materialIt was then dried over magnesium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated
9. distillationthe resultant oil-like product was purified by distillation under reduced pressure (130° C./12 mmHg)

ORD record

ord-c79690b4fafb4e81ad7c25f47c3730a1

Source dataset

uspto-grants-1995_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05422359