반응 #73508

반응 방정식

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

diethylzinc

diiodomethane

water

→

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

수율 26.0%

용매

DCM

toluene

반응 조건

후처리

1. 1
   온도The reaction medium is refluxed for 18 hours
2. 2
   추출extracted with DCM (3×100 mL)
3. 3
   세척washed successively with water (4×100 mL) and brine (100 mL)
4. 4
   건조dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue obtained
8. 8
   기타is purified by chromatography on a column of silica gel
9. 9
   세척eluting with a 95/5 cyclohexane/EtOAc mixture

실험 절차

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.

출처