Diethyl (cyanomethyl)phosphonate → 2-(2-Oxaspiro[3.3]heptan-6-ylidene)acetonitrile

Temperature

0 °C

To a solution of diethyl cyanomethylphosphonate (82 mg; 0.464 mmol) in THF (2 mL) at 0° C. under nitrogen was added potassium t-butoxide (0.51 mmol; 1M solution in THF) and the mixture was stirred at 0° C. for 1 hour. A solution of 2-oxaspiro[3.3]heptan-6-one (52 mg; 0.464 mmol) in THF (1 mL) was added. A precipitate formed and further THF (1 mL) was added to enhance the stirring. The reaction mixture was allowed to stir for 4 hours at ambient temperature. The reaction mixture was partitioned between saturated aqueous ammonium chloride (10 mL) and ethyl acetate (10 mL). The phases were separated and the aqueous phase was extracted with ethyl acetate (3×10 mL). The extracts were combined, dried (sodium sulfate), filtered and evaporated under reduced pressure. The material was purified by silica gel chromatography eluting with hexane/ethyl acetate (3:2) to give the product as a colorless oil (20 mg).

1. customA precipitate formed
2. stirringto stir for 4 hours at ambient temperature
3. customThe reaction mixture was partitioned between saturated aqueous ammonium chloride (10 mL) and ethyl acetate (10 mL)
4. customThe phases were separated
5. extractionthe aqueous phase was extracted with ethyl acetate (3×10 mL)
6. dry with materialdried (sodium sulfate)
7. filtrationfiltered
8. customevaporated under reduced pressure
9. customThe material was purified by silica gel chromatography
10. washeluting with hexane/ethyl acetate (3:2)

ORD record

ord-932f7d20e2b74bd9baac935b8fdf5b12

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962596B2