Diethyl Ether → HCID 54398507, compound

Temperature

0 °C

In THF (10 ml) was suspended sodium hydride (60%, 440 mg, 11.0 mmol), and to the mixture was added at −30° C. a solution of diethylphosphonoethyl acetate (2.47 g, 11.0 mmol) in THF (10 ml). The mixture was stirred at the same temperature for 30 minutes, and to the mixture was added at −30° C. a solution of 6-bromo-2-pyridinecarbaldehyde (1.86 g, 10.0 mmol) in THF (10 ml). While warming the temperature of the mixture from −30° C. to −10° C., the mixture was stirred for 1.5 hours. To the mixture was added diethylether (40 ml), and the mixture was washed with water (20 ml, 5 ml×2) and saturated brine (5 ml). The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue was added hexane (10 ml), and the mixture was cooled to 0° C. The precipitated insoluble materials were filtered, which were washed with hexane cooled to 0° C., and dried under reduced pressure to give ethyl 6-bromo-2-pyridineacrylate (2.00 g, 7.81 mmol, 78%). IR (KBr): 1717, 1703 cm−1.

1. temperatureWhile warming the temperature of the mixture from −30° C. to −10° C.
2. stirringthe mixture was stirred for 1.5 hours
3. washthe mixture was washed with water (20 ml, 5 ml×2) and saturated brine (5 ml)
4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. additionTo the residue was added hexane (10 ml)
7. filtrationThe precipitated insoluble materials were filtered
8. washwhich were washed with hexane
9. temperaturecooled to 0° C.
10. customdried under reduced pressure

ORD record

ord-1851ddf7a195416ab8c3e42ed87c052c

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06413947B1