反应 #50677

反应方程式

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

3-methyl-2-thiophenecarboxylic acid

oxalyl chloride

tin (IV) chloride

→

product

收率 25.2%

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

收率 25.2%

溶剂

water

DCM

反应条件

后处理

1. 1
   温度the reaction mixture was cooled to -10° C.
2. 2
   workup.ADDITIONwas added in three portions
3. 3
   workup.STIRRINGAfter stirring for 1 hour in the cooling bath
4. 4
   其他the layers separated
5. 5
   洗涤The organic phase was washed twice with 5% HCl (aq.)
6. 6
   干燥dried (MgSO4)
7. 7
   过滤Filtration and concentration
8. 8
   其他gave the crude product
9. 9
   其他Purification via preparative HPLC (silica gel, DCM)

实验过程

To a stirred solution consisting of 3-methyl-2-thiophenecarboxylic acid (21.0 g) in dry DCM (1.5 l) was added oxalyl chloride (21.0 ml) at room temperature under nitrogen. After stirring for 1 hour at room temperature, the reaction mixture was cooled to -10° C. and tin (IV) chloride (17.3 ml) was added. The resulting solution was stirred for 10 minutes (-10° C.) at which time 2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (31.3 g) was added in three portions. After stirring for 1 hour in the cooling bath, the reaction mixture was poured into cold water and the layers separated. The organic phase was washed twice with 5% HCl (aq.) and dried (MgSO4). Filtration and concentration gave the crude product. Purification via preparative HPLC (silica gel, DCM) afforded 12.5 g of the product as a solid, m.p. 221°-223° C.

来源