反应 #11248

反应方程式

( 859 )

7-Bromo-2-[(E)-2-(2-chlorophenyl)ethenyl]-5-methoxy-1-benzofuran

maleimide

maleimide

tin(II) chloride

tin(II) chloride

→

7-Bromo-4-(2-chlorophenyl)-9-methoxy-3a,4,5,10c-tetrahydro-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dione

溶剂

反应条件

后处理

1. 1
   温度was again heated to 150° C. overnight
2. 2
   其他The solid which formed
3. 3
   其他was collected
4. 4
   洗涤washed with xylenes (20 mL)
5. 5
   workup.DISSOLUTIONbefore dissolving in ethyl acetate (200 mL)
6. 6
   workup.ADDITIONWater (50 mL) was added
7. 7
   过滤the mixture was filtered through a pad of Celite
8. 8
   其他The resulting layers were separated
9. 9
   洗涤the organic phase was washed with brine (50 mL)
10. 10
    干燥dried over magnesium sulphate
11. 11
    过滤filtered
12. 12
    浓缩concentrated to dryness
13. 13
    其他The product (860) (6.1 g, 71%) was used without further purification

实验过程

A solution of (859) (4.89 g, 0.0185 mol) prepared as described in example 441, maleimide (1.44 g, 0.02 mol) and tin(II) chloride (2.8 g, 0.02 mol) in xylenes (40 mL) was heated to 150° C. overnight. After the addition of more maleimide (1.44 g, 0.02 mol) and tin(II) chloride (1.44 g, 0.01 mol) the reaction was again heated to 150° C. overnight. The solid which formed was collected and washed with xylenes (20 mL) before dissolving in ethyl acetate (200 mL). Water (50 mL) was added and the mixture was filtered through a pad of Celite. The resulting layers were separated, the organic phase was washed with brine (50 mL) dried over magnesium sulphate, filtered and concentrated to dryness. The product (860) (6.1 g, 71%) was used without further purification. 1H NMR δ (CDCl3) 7.60 (d, J=6.5 Hz, 1H), 7.40 (m, 2H), 7.25 (m, 1H), 7.1 (m, 2H), 4.36 (dd, J=7.3, 1 Hz, 1H), 4.0 (m, 1H), 3.86 (s, 3H), 3.81 (m, 1H), 3.45 (m, 1H), 3.10 (dd, J=4.7, 17 Hz, 1H); MH+:462,460.

来源