Reaktion #415021

Reaktionsgleichung

2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione

acetyl chloride

tin (IV) chloride

→

product

2-(2-Acetyl-1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe temperature below 0° C
2. 2
   SonstigeThe layers were separated
3. 3
   Extraktionthe aqueous phase was extracted with DCM
4. 4
   WaschenThe combined organics were washed twice with 5% HCl (aq.)
5. 5
   Trocknendried (MgSO4)
6. 6
   FiltrationFiltration and concentration
7. 7
   Sonstigegave the crude product
8. 8
   SonstigePurification via flash column chromatography (silica gel, DCM)

Vorschrift

To a stirred solution of acetyl chloride (6.77 ml) in DCM (400 ml) was added tin (IV) chloride (11.14 ml) at -5° C., under nitrogen. 2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (20.0 g) was then added portion-wise, keeping the temperature below 0° C. The reaction mixture was then stirred at 0° C. for 0.5 hour, at which time it was poured into ice water. The layers were separated and the aqueous phase was extracted with DCM. The combined organics were washed twice with 5% HCl (aq.) and dried (MgSO4). Filtration and concentration gave the crude product. Purification via flash column chromatography (silica gel, DCM) afforded 9.62 g of the product as a solid, m.p. 204°-205° C.

Quelle