Reaktion #410474

Reaktionsgleichung

methyl phenylacetate

lithium diisopropylamide

α-bromoacetonitrile

→

title compound

methyl 3-cyano-2-phenylpropionate

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturCool in a dry-ice/acetone bath
2. 2
   workup.WAITAfter 2 hours
3. 3
   Sonstigepartition the reaction mixture between ethyl acetate and water
4. 4
   SonstigeSeparate the aqueous layer
5. 5
   Extraktionextract three times with ethyl acetate
6. 6
   TrocknenDry the combined organic layers over Na2SO4
7. 7
   Filtrationfilter
8. 8
   Einengenconcentrate in vacuo
9. 9
   Sonstigeto obtain a residue
10. 10
    workup.DISTILLATIONDistill the residue bulb-to-bulb

Vorschrift

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).

Quelle