반응 #50683

반응 방정식

water

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

isobutyryl chloride

tin (IV) chloride

→

product

2-[2-(2-Methyl-1-oxopropyl)-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dione

용매

DCM

반응 조건

후처리

1. 1
   workup.ADDITIONwas added portion-wise
2. 2
   기타The layers were separated
3. 3
   세척the organic phase was washed twice with water, once with 5% HCl (aq.)
4. 4
   건조subsequently dried (MgSO4)
5. 5
   여과Filtration and concentration
6. 6
   기타gave the crude product
7. 7
   기타Purification via preparative HPLC (silica gel, DCM)

실험 절차

To a stirred solution of isobutyryl chloride (5.4 ml) in DCM (250 ml) was added tin (IV) chloride (5.8 ml) at -10° C. under nitrogen. After stirring for 15 minutes in the cooling bath, 2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (10.0 g) was added portion-wise. The reaction mixture was allowed to warm to room temperature, and stir for three days, at which time it was poured into cold water. The layers were separated and the organic phase was washed twice with water, once with 5% HCl (aq.), and subsequently dried (MgSO4). Filtration and concentration gave the crude product. Purification via preparative HPLC (silica gel, DCM) afforded 2.5 g of the product as a solid, m.p. 147°-149° C.

출처