反応 #73508

反応方程式

methyl 2-acetyl-3-phenylbut-3-enoate

diethylzinc

diiodomethane

water

→

methyl 3-oxo-2(1-phenylcyclopropyl)butanoate

収率 26.0%

溶媒

DCM

toluene

反応条件

後処理

1. 1
   温度The reaction medium is refluxed for 18 hours
2. 2
   抽出extracted with DCM (3×100 mL)
3. 3
   洗浄washed successively with water (4×100 mL) and brine (100 mL)
4. 4
   乾燥dried over Na2SO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他The residue obtained
8. 8
   その他is purified by chromatography on a column of silica gel
9. 9
   洗浄eluting with a 95/5 cyclohexane/EtOAc mixture

実験手順

To a solution of 1 g (4.6 mmol) of methyl 2-acetyl-3-phenylbut-3-enoate in 16 mL of DCM are successively added dropwise 20.8 mL (22.9 mmol) of a 1.1M solution of diethylzinc in toluene and 3.7 mL (45.8 mmol) of diiodomethane. The reaction medium is refluxed for 18 hours. After cooling to room temperature, the reaction mixture is treated with 100 mL of water and then extracted with DCM (3×100 mL). The organic phases are combined, washed successively with water (4×100 mL) and brine (100 mL), dried over Na2SO4, filtered and then concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a 95/5 cyclohexane/EtOAc mixture. 280 mg of methyl 3-oxo-2(1-phenylcyclopropyl)butanoate are obtained in the form of a yellow oil.

出典