Phenylacetonitrile → Diethyl [cyano(phenyl)methyl]phosphonate

Temperature

-78 °C

To a stirred solution of benzyl cyanide (2.5 g) in dry tetrahydrofuran (25 mL), slowly added lithium hexamethyl disilazane (26 mL, 1.0M in THF) under nitrogen atmosphere at −78° C. The reaction mixture was stirred at −78° C. for 1 hour and chloro diethyl phosphite (5 g) was added slowly under nitrogen atmosphere at −78° C. The reaction mixture was stirred at −78° C. for about 2 hours and quenched with saturated ammonium chloride solution (25 mL). The reaction mixture was diluted with ethyl acetate (50 mL) and aqueous layer was extracted with ethyl acetate (2×25 mL). The combined organic layer was washed with brine (50 mL) and dried over anhydrous Na2SO4. Evaporation of solvent under reduced pressure gave crude diethyl cyano(phenyl)methylphosphonate (3 g) as yellow liquid, which was used without any purification. 1H NMR (CDCl3): δ 1.24-1.28 (t, 3H), 1.30-1.33 (t, 3H), 4.14-3.90 (m, 4H), 4.20 (d, 1H), δ 7.45-7.20 (m, 5H).

1. customat −78° C
2. stirringThe reaction mixture was stirred at −78° C. for about 2 hours
3. customquenched with saturated ammonium chloride solution (25 mL)
4. additionThe reaction mixture was diluted with ethyl acetate (50 mL) and aqueous layer
5. extractionwas extracted with ethyl acetate (2×25 mL)
6. washThe combined organic layer was washed with brine (50 mL)
7. dry with materialdried over anhydrous Na2SO4
8. customEvaporation of solvent under reduced pressure

ORD record

ord-3014693cb862461b9cd1bf303cb3376c

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193725B2