Реакция #2809

Уравнение реакции

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

ozone

→

title compound

Выход 100.0%

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

Выход 100.0%

Растворители

methylene chloride

methanol

Условия реакции

Обработка

1. 1
   ДругоеPurge with nitrogen
2. 2
   workup.ADDITIONadd dimethylsulfide (7 mL) and pyridine (0.35 mL)
3. 3
   ТемператураAllow to warm to room temperature gradually overnight
4. 4
   ДругоеPartition between methylene chloride (100 mL) and water (40 mL)
5. 5
   ЭкстракцияExtract the aqueous with methylene chloride (50 mL)
6. 6
   Другоеdry (Na2 SO4)
7. 7
   Другоеpurify by silica gel chromatography (2.5:1 hexane/ethyl acetate)

Методика

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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