반응 #11248

반응 방정식

( 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

용매

반응 조건

후처리

1. 1
   온도was again heated to 150° C. overnight
2. 2
   기타The solid which formed
3. 3
   기타was collected
4. 4
   세척washed with xylenes (20 mL)
5. 5
   workup.DISSOLUTIONbefore dissolving in ethyl acetate (200 mL)
6. 6
   workup.ADDITIONWater (50 mL) was added
7. 7
   여과the mixture was filtered through a pad of Celite
8. 8
   기타The resulting layers were separated
9. 9
   세척the organic phase was washed with brine (50 mL)
10. 10
    건조dried over magnesium sulphate
11. 11
    여과filtered
12. 12
    농축concentrated to dryness
13. 13
    기타The product (860) (6.1 g, 71%) was used without further purification

실험 절차

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.

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