Acetonitrile → 4-(Benzyloxy)-3-oxobutanenitrile

Temperature

-78 °C

In a stream of argon, 156.2 ml (0.248 mole) of a solution of 1.6 moles of n-butyllithiumhexane was added to 150 ml of anhydrous tetrahydrofuran. The mixture was cooled to -78° C., and a solution of 15.8 ml (0.293 mole) of acetonitrile in 50 ml of anhydrous tetrahydrofuran was added dropwise. The mixture was stirred at -78° C. for 1 hour. A solution of 55.2 g (0.248 mole) of ethylbenzyloxyacetate in 100 ml of anhydrous tetrahydrofuran was added dropwise. The mixture was stirred at -78° C. for 15 minutes and at room temperature for 50 minutes. The mixture was then poured into 200 ml of ice water. The aqueous layer was washed with ether, acidified with concentrated hydrochloric acid, and extracted with ether. The ether layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 70.9 g of crude 4-benzyloxy-3-ketobutanenitrile.

1. stirringThe mixture was stirred at -78° C. for 15 minutes and at room temperature for 50 minutes
2. washThe aqueous layer was washed with ether
3. extractionextracted with ether
4. washThe ether layer was washed with water
5. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
6. customThe solvent was evaporated under reduced pressure

ORD record

ord-ccf9c7b1ace64bb5a0e08062d3a41f33

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04874760