Reaktion #10995

Reaktionsgleichung

Allyl 3-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

p-toluenesulfonic acid anhydride

→

desired product

Allyl 2-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate

Lösungsmittel

acetone water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the obtained solution
2. 2
   Waschenthe reaction mixture was washed with water
3. 3
   Sonstigeacetone was removed
4. 4
   workup.DISTILLATIONby distilling under a reduced pressure
5. 5
   ExtraktionThe residue was extracted with dichloromethane
6. 6
   TrocknenThe combined organic layer was dried with anhydrous sulfate
7. 7
   workup.DISTILLATIONdistilled under a reduced pressure

Vorschrift

Allyl 3-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (331 mg, 0.91 mmol) was dissolved in a a solvent mixture of acetone/water (v/v=5/1), and catalyst amount of p-toluenesulfonic acid anhydride was added to the obtained solution. The resulting mixture was refluxed at 80° C. for 18 hours. After the reaction was completed, the reaction mixture was washed with water, and then acetone was removed by distilling under a reduced pressure. The residue was extracted with dichloromethane. The combined organic layer was dried with anhydrous sulfate and distilled under a reduced pressure. The desired product was obtained (131.2 mg, 31%) by performing column chromatography (eluent: n-hexane/ethyl acetate=2/1).

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