Furan → 2-Pentadecylfuran

Temperature

-78 °C

A dry 50 ml round bottom flask charged with furan (1.40 g, 20.6 mmol) and THF (10 ml), was cooled to -78° C. and n-butyllithium (13.6 ml, 1.50 M in hexanes, 20.6 mmol) was added dropwise. The solution was stirred for 30 mm at -78° C., then warmed to 0° C. and placed in an ice bath for 1 h. The mixture was then cooled to -78° C. and 1-bromopentadecane 9 (5 g, 17.2 mmol) in THF (10 ml) were added dropwise. The resulting solution was stirred for 1 h, then warmed to room temp and stirred 12 h. The reaction was quenched with a saturated solution of NH4Cl (5 ml). The organic layer was separated and the aqueous layer extracted with ether (3×20 ml). The combined organic layers were washed with saturated NaHCO3 (1×20 ml), brine (1×20 ml), dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by flash chromatography on silica, eluting with hexanes to afford a oily liquid that was recrystallized from methanol (~ 50 ml/g, cooling to 5° C.) to afford 4.8 g (64%) of 2-(pentadecyl)furan (1).

1. temperaturewarmed to 0° C.
2. temperatureThe mixture was then cooled to -78° C.
3. stirringThe resulting solution was stirred for 1 h
4. temperaturewarmed to room temp
5. stirringstirred 12 h
6. customThe reaction was quenched with a saturated solution of NH4Cl (5 ml)
7. customThe organic layer was separated
8. extractionthe aqueous layer extracted with ether (3×20 ml)
9. washThe combined organic layers were washed with saturated NaHCO3 (1×20 ml), brine (1×20 ml)
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated under vacuum
13. customThe crude product was purified by flash chromatography on silica
14. washeluting with hexanes
15. customto afford a oily liquid that
16. customwas recrystallized from methanol (~ 50 ml/g, cooling to 5° C.)

ORD record

ord-6bd1cd534bcd493bbedc469f56adeaba

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06133313