Reacción #410474

Ecuación de reacción

methyl phenylacetate

lithium diisopropylamide

α-bromoacetonitrile

→

title compound

methyl 3-cyano-2-phenylpropionate

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaCool in a dry-ice/acetone bath
2. 2
   workup.WAITAfter 2 hours
3. 3
   Otropartition the reaction mixture between ethyl acetate and water
4. 4
   OtroSeparate the aqueous layer
5. 5
   Extracciónextract three times with ethyl acetate
6. 6
   SecadoDry the combined organic layers over Na2SO4
7. 7
   Filtraciónfilter
8. 8
   Concentraciónconcentrate in vacuo
9. 9
   Otroto obtain a residue
10. 10
    workup.DISTILLATIONDistill the residue bulb-to-bulb

Procedimiento

Combine methyl phenylacetate (2.0 g, 13.32 mmol) and tetrahydrofuran (15 mL). Cool in a dry-ice/acetone bath. Add dropwise a solution of lithium diisopropylamide (6.66 mL, 2 M in THF, 13.32 mmol). After 1 hour, add α-bromoacetonitrile (1.6 g, 13.32 mmol). After 2 hours, warm the reaction mixture to ambient temperature and partition the reaction mixture between ethyl acetate and water. Separate the aqueous layer and extract three times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Distill the residue bulb-to-bulb to give the title compound: bp; 150° C. at 0.5 mm Hg; Rf=0.72 (silica gel, 25% ethyl acetate/hexane).

Fuente