反応 #357345

反応方程式

acetophenone

ethyl cyanoacetate

acetic

ammonium acetate

ethyl cyanoacetate

ammonium acetate

→

2-Cyano-3-phenyl-but-2-enoic acid ethyl ester

溶媒

benzene

ethyl acetate

acetic acid

反応条件

後処理

1. 1
   温度to reflux in a Dean-Stark apparatus
2. 2
   workup.WAITAfter an additional 10 hours
3. 3
   洗浄washed with water (240 mL), brine (40 mL)
4. 4
   その他dried (Na2S04)
5. 5
   ろ過After filtering
6. 6
   濃縮the extract was concentrated in vacuo
7. 7
   workup.ADDITIONthe desired product, as a mixture of E and Z-isomers
8. 8
   その他was isolated by column chromatography on silica gel
9. 9
   洗浄eluting with 5% ethyl acetate in petroleum ether
10. 10
    その他affording an oil that
11. 11
    その他on standing at room temperature

実験手順

A mixture of acetophenone (50 mmol), ethyl cyanoacetate (50 mmol), acetic; acid (1.14 mL), ammonium acetate (400 mg), and benzene (50 mL) was heated to reflux in a Dean-Stark apparatus. After approximately 10 hours, additional ethyl cyanoacetate (50 mmol), acetic acid (1.14 mL), and ammonium acetate (400 mL) are added. After an additional 10 hours, the reaction was cooled to room temperature, diluted with ethyl acetate (30 mL), washed with water (240 mL), brine (40 mL), and dried (Na2S04). After filtering, the extract was concentrated in vacuo and the desired product, as a mixture of E and Z-isomers, was isolated by column chromatography on silica gel, eluting with 5% ethyl acetate in petroleum ether, affording an oil that solidified on standing at room temperature.

出典