Reaktion #573669

Reaktionsgleichung

methyl 2-phenyl-acrylate

Lithium diisopropylamide

acetonitrile

ammonium chloride

→

title compound

Ausbeute 75.0%

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

Ausbeute 75.0%

Lösungsmittel

cyclohexane

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting mixture was partitioned between ethyl acetate and water
2. 2
   Trocknenthe organic phase dried over magnesium sulphate
3. 3
   Sonstigeevaporated
4. 4
   Sonstigeto give a residue which
5. 5
   Sonstigewas partitioned between ether and 10% aqueous sodium carbonate
6. 6
   TrocknenThe organic layer was dried over magnesium sulphate
7. 7
   Sonstigeevaporated

Vorschrift

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.

Quelle