Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N+:13]([O-:15])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:26]([CH2:32][CH2:33][CH:34]=[O:35])([CH:29]([CH3:31])[CH3:30])[C:27]#[N:28])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25].[F-].[K+]>CC(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([N+:13]([O-:15])=[O:14])[CH:34]([OH:35])[CH2:33][CH2:32][C:26]([C:27]#[N:28])([CH:29]([CH3:30])[CH3:31])[C:20]2[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:18]([O:17][CH3:16])[CH:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of 2-(3,4-dimethoxyphenyl)-1-nitroethane (4, 135 g, 0.64 mol), 2-(3,4-dimethoxyphenyl)-2-(3-oxopropyl)-2-isopropylacetonitrile (7, 156 g, 0.57 mol) and KF (19.3 g, anhydrous, Aldrich) in 2-propanol (2.0 L) was heated to 50°-55° C. for about 40 hours. The mixture was then cooled to room temperature and the isopropanol removed in vacuo. The residue was dissolved in CH2Cl2 (1.6 L) and filtered through Celite (50 g). The filtrate was extracted with saturated aqueous NaHCO3 (2×500 mL), the organic layer evaporated, and the product recrystallized from ethyl acetate-hexane (1:1) to yield 1-(3,4-dimethoxyphenyl)-2-nitro-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)-hexan-3-ol (8, 205 g, m.p. 171°-173° C., MS m/e 486(M+)).
Aufarbeitung
- temperaturewas heated to 50°-55° C. for about 40 hours
- customthe isopropanol removed in vacuo
- dissolutionThe residue was dissolved in CH2Cl2 (1.6 L)
- filtrationfiltered through Celite (50 g)
- extractionThe filtrate was extracted with saturated aqueous NaHCO3 (2×500 mL)
- customthe organic layer evaporated
- customthe product recrystallized from ethyl acetate-hexane (1:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-92b6f07b7f574e82a63201563d3f281b
- Quelldatensatz
- uspto-grants-1986_09
- Patentnummer
- US04613606
Verknüpfte Notizen
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