Hydroxylamine, O-((4-nitrophenyl)methyl)-, hydrochloride (1:1) → (E)-1-(4-methoxy-3-propan-2-yloxyphenyl)-N-[(4-nitrophenyl)methoxy]ethanimine
Reaktionsgleichung
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:13](=O)[CH3:14])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])([CH3:3])[CH3:2].Cl.[N+:17]([C:20]1[CH:28]=[CH:27][C:23]([CH2:24][O:25][NH2:26])=[CH:22][CH:21]=1)([O-:19])=[O:18]>>[N+:17]([C:20]1[CH:21]=[CH:22][C:23]([CH2:24][O:25]/[N:26]=[C:13](/[C:7]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:6]=2)\[CH3:14])=[CH:27][CH:28]=1)([O-:19])=[O:18]Komponenten
3
Versuchsvorschrift
3′-Isopropoxy-4′-methoxyacetophenone (8) (150 mg, 0.720 mmol) was condensed with compound 19 (162 mg, 0.792 mmol) according to the general procedure II-A defined above. After being heated for 3 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing yellow oil was dissolved in CH2Cl2 (20 mL) and the resulting solution washed with H2O (2×15 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (15:85 v/v ethyl acetate/hexane elution) to afford the title compound CP30254 (229 mg, 89%) as a pale-yellow oil, which solidified upon extensive standing, m.p. 44.5-46.1° C., Rf 0.5 in 1:1 v/v ethyl acetate/hexane.