반응 #50679

반응 방정식

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

용매

DCM

반응 조건

후처리

1. 1
   기타the temperature below 0° C
2. 2
   기타The layers were separated
3. 3
   추출the aqueous phase was extracted with DCM
4. 4
   세척The combined organics were washed twice with 5% HCl (aq.)
5. 5
   건조dried (MgSO4)
6. 6
   여과Filtration and concentration
7. 7
   기타gave the crude product
8. 8
   기타Purification via flash column chromatography (silica gel, DCM)

실험 절차

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.

출처