反応 #410474

反応方程式

methyl phenylacetate

lithium diisopropylamide

α-bromoacetonitrile

→

title compound

methyl 3-cyano-2-phenylpropionate

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度Cool in a dry-ice/acetone bath
2. 2
   workup.WAITAfter 2 hours
3. 3
   その他partition the reaction mixture between ethyl acetate and water
4. 4
   その他Separate the aqueous layer
5. 5
   抽出extract three times with ethyl acetate
6. 6
   乾燥Dry the combined organic layers over Na2SO4
7. 7
   ろ過filter
8. 8
   濃縮concentrate in vacuo
9. 9
   その他to obtain a residue
10. 10
    workup.DISTILLATIONDistill the residue bulb-to-bulb

実験手順

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).

出典