Reaktion #2809

Reaktionsgleichung

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

ozone

→

title compound

Ausbeute 100.0%

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

Ausbeute 100.0%

Lösungsmittel

methylene chloride

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigePurge with nitrogen
2. 2
   workup.ADDITIONadd dimethylsulfide (7 mL) and pyridine (0.35 mL)
3. 3
   TemperaturAllow to warm to room temperature gradually overnight
4. 4
   SonstigePartition between methylene chloride (100 mL) and water (40 mL)
5. 5
   ExtraktionExtract the aqueous with methylene chloride (50 mL)
6. 6
   Sonstigedry (Na2 SO4)
7. 7
   Sonstigepurify by silica gel chromatography (2.5:1 hexane/ethyl acetate)

Vorschrift

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%).

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