3-Furancarboxamide,tetrahydro-N-methoxy-N-methyl-(9CI) → HCID 21702750, compound

Temperature

0 °C

Into a 250-mL 3-neck round-bottom flask, was placed a solution of N-methoxy-N-methyltetrahydrofuran-3-carboxamide (compound 263.1, 6.71 g, 42.2 mmol) in tetrahydrofuran (100 mL). The system was purged with nitrogen, then cooled to 0° C. Ethylmagnesium bromide (3M in diethyl ether, 17 mL, 51 mmol) was added drop-wise at 0° C. over 30 min. The resulting solution was stirred overnight at 40° C., then cooled and carefully quenched with aqueous HCl (1M, 10 mL). The resulting mixture was concentrated under reduced pressure and the residue was diluted with water (10 mL). The mixture was extracted with ethyl acetate (3×30 mL) and the combined organic extracts were washed with brine (2×10 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. Obtained the title compound as a light yellow oil (4.5 g, 83%).

1. customInto a 250-mL 3-neck round-bottom flask, was placed
2. customThe system was purged with nitrogen
3. temperaturecooled
4. customcarefully quenched with aqueous HCl (1M, 10 mL)
5. concentrationThe resulting mixture was concentrated under reduced pressure
6. additionthe residue was diluted with water (10 mL)
7. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
8. washthe combined organic extracts were washed with brine (2×10 mL)
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure

ORD record

ord-2822da7dd25c4ff09cc8fcfb5a8309b2

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2