Diethyl Ether → 3-butylfuran

Temperature

-78 °C

The iodo-product obtained from Step B above (2.2 g, 8.8 mmol) was dissolved in 60 mL of ether, and stirred in a −78° C. bath. A 1.7 M solution of t-butyllithium in pentane (10.4 mL, 17.7 mmol) was added dropwise. After 20 min, cooling bath was removed. Reaction was continued for 2.5 h, and quenched with H2O (20 mL). The aqueous mixture was stirred overnight and separated. The aqueous layer was extracted with ether (30 mL). The combined organic layers were washed with brine, dried by Na2SO4, and filtered through a Celite pad. Removal of solvent gave 1.10 g (100%) of 3-butylfuran as a reddish-yellow oil.

1. temperaturecooling bath
2. customwas removed
3. customReaction
4. waitwas continued for 2.5 h
5. customquenched with H2O (20 mL)
6. stirringThe aqueous mixture was stirred overnight
7. customseparated
8. extractionThe aqueous layer was extracted with ether (30 mL)
9. washThe combined organic layers were washed with brine
10. dry with materialdried by Na2SO4
11. filtrationfiltered through a Celite pad
12. customRemoval of solvent

ORD record

ord-4aca72a60a914c6e9a53ecdf468ef59b

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964646B2