反応 #11248

反応方程式

( 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

溶媒

反応条件

後処理

1. 1
   温度was again heated to 150° C. overnight
2. 2
   その他The solid which formed
3. 3
   その他was collected
4. 4
   洗浄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
   ろ過the mixture was filtered through a pad of Celite
8. 8
   その他The resulting layers were separated
9. 9
   洗浄the organic phase was washed with brine (50 mL)
10. 10
    乾燥dried over magnesium sulphate
11. 11
    ろ過filtered
12. 12
    濃縮concentrated to dryness
13. 13
    その他The product (860) (6.1 g, 71%) was used without further purification

実験手順

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.

出典