Hydracrylonitrile → 2-Cyanoethyl prop-2-ynoate

Temperature

-20 °C

2.71 mg (44 mmol) of propiolic acid and 2.73 ml (40 mmol) of 2-cyanoethanol were dissolved in 20 ml of dry ether. The obtained solution was cooled to −20° C. 100 ml of a solution of 9.27 g (45 mmol) of dicyclohexylcarbodiimide and 0.36 g (30 mmol) of 4-dimethylaminopyridine in dry ether was dropped into the solution. The temperature of the obtained mixture was elevated to room temperature. After stirring overnight, the insoluble matter was filtered out. The filtrate was washed with 2 N hydrochloric acid and saturated aqueous salt solution, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (ethyl acetate) to obtain the title compound.

1. customwas elevated to room temperature
2. filtrationthe insoluble matter was filtered out
3. washThe filtrate was washed with 2 N hydrochloric acid and saturated aqueous salt solution
4. dry with materialdried over anhydrous sodium sulfate
5. customThe solvent was evaporated under reduced pressure
6. customthe residue was purified by the silica gel chromatography (ethyl acetate)

ORD record

ord-ea33498b0a7440eb99154ce1e1f3a60e

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06995179B2