Furan → HCID 67697278, compound

Temperature

-78 °C

To a solution of furan (10.7 mL, 0.147 mol) in 100 mL of THF at 0° C. was added n-butyllithium (65 mL, 0.149 mol). The reaction was stirred 3 h and was cooled to -78° C. To the reaction flask was then slowly added 2-methoxy-ethoxymethylchloride (16.8 mL, 0.147 mol) in 100 mL THF. The solution was warmed to -20° C. and allowed to stir until the solution was clear. It was then quenched with saturated ammonium chloride solution (50mL) and the aqueous layer was washed with ethyl acetate (3×, 50 mL). The combined organic layer was washed with brine, dried (MgSO4), filtered and evaporated to yield 18 g of crude product. Distillation under high vacuum yielded 14.5 g (63%) of 2-methoxyethoxy-methylfuran.

1. temperatureThe solution was warmed to -20° C.
2. stirringto stir until the solution
3. customIt was then quenched with saturated ammonium chloride solution (50mL)
4. washthe aqueous layer was washed with ethyl acetate (3×, 50 mL)
5. washThe combined organic layer was washed with brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customevaporated
9. customto yield 18 g of crude product
10. distillationDistillation under high vacuum

ORD record

ord-d0ce77d66da94f0daea0b63943b621b8

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05112848