Реакция #410474

Уравнение реакции

methyl phenylacetate

lithium diisopropylamide

α-bromoacetonitrile

→

title compound

methyl 3-cyano-2-phenylpropionate

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   ТемператураCool in a dry-ice/acetone bath
2. 2
   workup.WAITAfter 2 hours
3. 3
   Другоеpartition the reaction mixture between ethyl acetate and water
4. 4
   ДругоеSeparate the aqueous layer
5. 5
   Экстракцияextract three times with ethyl acetate
6. 6
   СушкаDry the combined organic layers over Na2SO4
7. 7
   Фильтрацияfilter
8. 8
   Концентрированиеconcentrate in vacuo
9. 9
   Другоеto obtain a residue
10. 10
    workup.DISTILLATIONDistill the residue bulb-to-bulb

Методика

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).

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