반응 #2809

반응 방정식

2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid, 2-trimethylsilanyl-ethyl ester

ozone

→

title compound

수율 100.0%

2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-formyl-phenyl)-propionic acid, 2-trimethylsilanyl-ethyl ester

수율 100.0%

용매

methylene chloride

methanol

반응 조건

후처리

1. 1
   기타Purge with nitrogen
2. 2
   workup.ADDITIONadd dimethylsulfide (7 mL) and pyridine (0.35 mL)
3. 3
   온도Allow to warm to room temperature gradually overnight
4. 4
   기타Partition between methylene chloride (100 mL) and water (40 mL)
5. 5
   추출Extract the aqueous with methylene chloride (50 mL)
6. 6
   기타dry (Na2 SO4)
7. 7
   기타purify by silica gel chromatography (2.5:1 hexane/ethyl acetate)

실험 절차

Dissolve 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid, 2-trimethylsilanyl-ethyl ester (2.61 g, 6.19 mmol) in methylene chloride (70 mL) and methanol (75 mL). Cool to -78° C. and treat with ozone until a blue color persists. Purge with nitrogen and add dimethylsulfide (7 mL) and pyridine (0.35 mL). Allow to warm to room temperature gradually overnight. Partition between methylene chloride (100 mL) and water (40 mL). Extract the aqueous with methylene chloride (50 mL), dry (Na2 SO4) and purify by silica gel chromatography (2.5:1 hexane/ethyl acetate) to give the title compound as a colorless viscous oil (2.65 g, 100%).

출처