2-Methoxy-1,3-butadiene → 3,4,4a, 12a-Tetrahydro-11-chloro-6,7-dihydroxy-2,5,12(1H)-naphthacenetrione
Reaktionsgleichung
[Cl:1][C:2]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[C:9]([OH:17])=[C:8]2[C:3]=1[C:4](=[O:19])[CH:5]=[CH:6][C:7]2=[O:18].C[O:21][C:22]([CH:24]=[CH2:25])=[CH2:23]>C1C=CC=CC=1>[Cl:1][C:2]1[C:15]2[C:10]([C:9]([OH:17])=[C:8]3[C:3]=1[C:4](=[O:19])[CH:5]1[CH:6]([CH2:25][CH2:24][C:22](=[O:21])[CH2:23]1)[C:7]3=[O:18])=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
10-Chloro-8,9-dihydroxy-1,4-anthracenedione (compound 3) (100 mg), 2-methoxy-1,3-butadiene (564 mg) and dry benzene (10 ml) were heated in a sealed tube for 4 h at 130°. After cooling the crude solution was preparatively chromatographed on silica gel layers containing oxalic acid (2%) with chloroform as eluant. The major yellow band was recovered to give the product (compound 9) as a yellow crystalline solid (85 mg, 68%).