Diethyl (cyanomethyl)phosphonate → HCID 67451464, compound

To a solution of diethyl cyanomethylphosphonate (4.09 g; 23.1 mmol) in dry THF (200 mL) at 0° C. under nitrogen was added potassium t-butoxide (23.1 mmol; 1M solution in THF). The mixture was stirred for 1 hour. The solution of 2,2-difluorocyclopropanecarbaldehyde from Step A was added and the mixture was stirred while allowing to warm to ambient temperature. A portion of the solvent was removed under reduced pressure and the remaining solution was diluted with ammonium chloride solution (50 mL). The mixture was extracted into ethyl acetate (2×50 mL). The combined extracts were dried (magnesium sulfate and sodium sulfate), filtered and evaporated under reduced pressure. The material was purified by chromatography on silica gel, eluting with hexane/ethyl acetate (3:1) to give 3-(2,2-difluorocyclopropyl)acrylonitrile (0.50 g) as a pale yellow oil (containing some ethyl acetate).

1. stirringthe mixture was stirred
2. customA portion of the solvent was removed under reduced pressure
3. additionthe remaining solution was diluted with ammonium chloride solution (50 mL)
4. extractionThe mixture was extracted into ethyl acetate (2×50 mL)
5. dry with materialThe combined extracts were dried (magnesium sulfate and sodium sulfate)
6. filtrationfiltered
7. customevaporated under reduced pressure
8. customThe material was purified by chromatography on silica gel
9. washeluting with hexane/ethyl acetate (3:1)

ORD record

ord-ab1f4c180f45419590f13cc6e90e8de6

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962596B2