Reacción #573669

Ecuación de reacción

methyl 2-phenyl-acrylate

Lithium diisopropylamide

acetonitrile

ammonium chloride

→

title compound

Rendimiento 75.0%

Methyl (RS)-4-cyano-2-Phenylbutanoate

Rendimiento 75.0%

Disolventes

cyclohexane

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting mixture was partitioned between ethyl acetate and water
2. 2
   Secadothe organic phase dried over magnesium sulphate
3. 3
   Otroevaporated
4. 4
   Otroto give a residue which
5. 5
   Otrowas partitioned between ether and 10% aqueous sodium carbonate
6. 6
   SecadoThe organic layer was dried over magnesium sulphate
7. 7
   Otroevaporated

Procedimiento

Lithium diisopropylamide (3.67 ml of a 1.5 molar solution in cyclohexane) was added to acetonitrile (0.26 ml) in tetrahydrofuran (10 ml) at -78° C. After 1 hour, methyl 2-phenyl-acrylate (see Preparation 22) (0.81 g) in tetrahydrofurn (10 ml) was added and the mixture was stirred for 1 hour, allowed to warm to room temperature then treated with saturated ammonium chloride solution. The resulting mixture was partitioned between ethyl acetate and water, the organic phase dried over magnesium sulphate and evaporated to give a residue which was partitioned between ether and 10% aqueous sodium carbonate. The organic layer was dried over magnesium sulphate and evaporated to leave the title compound (0.5 g, 75%) as an oil.

Fuente