Acetonitrile → 3-(4-Ethoxyphenyl)-3-oxopropanenitrile

Temperature

-78 °C

Under Ar(g), a solution of anhydrous acetonitrile (1.5 mL) in 35 mL anhydrous THF is cooled to −78° C. in a dry ice-acetone bath and then slowly treated with 11 mL of a 2.5 M n-butyl lithium in hexanes. The reaction mixture is maintained at −78° C. for an additional 45 min. and then slowly treated with a solution of 5 gms. of 4-ethoxy-benzoic acid ethyl ester in 5 mL of anhydrous THF. The resulting solution is then stirred overnight at room temperature. Subsequently, the reaction mixture is treated with 10% NaOH(aq) to dissolve solids and then extracted with ethyl acetate. The aqueous layer is acidified (pH 6) with HCl(aq) affording a white precipitate which subsequently is filtered. The organic layer is concentrated in vacuo and the residue is triturated with isopropanol resulting in the formation of additional white precipitate. The combined precipitates provide the desired 3-(4-ethoxy-phenyl)-3-oxo-propionitrile in the amount of 2.5463 gms.

1. additionslowly treated with a solution of 5 gms
2. dissolutionto dissolve solids
3. extractionextracted with ethyl acetate
4. customaffording a white precipitate which
5. filtrationsubsequently is filtered
6. concentrationThe organic layer is concentrated in vacuo
7. customthe residue is triturated with isopropanol resulting in the formation of additional white precipitate
8. customThe combined precipitates

ORD record

ord-bea4cef94e674238a4475f922ee339e4

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06559173B1