Reaktionsgleichung
C1C=C(C(O)=[O:8])C(C(OO)=O)=CC=1.[C:14]1([S:20][CH2:21][C:22]2[NH:23][C:24]([CH3:47])=[C:25]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([N+:39]([O-:41])=[O:40])[CH:34]=3)[C:27]=2[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+]>CCOC(C)=O>[C:14]1([S:20]([CH2:21][C:22]2[NH:23][C:24]([CH3:47])=[C:25]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([N+:39]([O-:41])=[O:40])[CH:34]=3)[C:27]=2[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:8])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of monoperphtalic acid in AcOEt (0.37 M solution; 20 ml) is added at 0° C. to a mixture of 2-(phenylthio)methyl-3, 5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine (3.5 g) and NaHCO3 (3 g) in AcOEt (20 ml). After 30 minutes the mixture is filtered and the eluate is washed with 1N solution of sodium thiosulfate (2 ×10 ml), with a saturated solution of NaHCO3 (2×20 ml) and then with water (3×10 ml). The organic layer is dried on Na2SO4 and evaporated to dryness; the residue is purified by chromatography on SiO2 (hexane/AcOEt 85/15, as eluent) to give 3.5 g of 2-(phenylsulfinyl)methyl-3,5-dicarboethoxy-4-(m-nitrophenyl) -6-methyl-1,4-dihydropyridine, m.p. 160°-162° C.
Aufarbeitung
- filtrationAfter 30 minutes the mixture is filtered
- washthe eluate is washed with 1N solution of sodium thiosulfate (2 ×10 ml), with a saturated solution of NaHCO3 (2×20 ml)
- customThe organic layer is dried on Na2SO4
- customevaporated to dryness
- customthe residue is purified by chromatography on SiO2 (hexane/AcOEt 85/15, as eluent)
Quellen und Nachweise
- ORD-Eintrag
- ord-ce929d93de2e4375bbe94fc1fd258f7b
- Quelldatensatz
- uspto-grants-1991_03
- Patentnummer
- US04999362
Verknüpfte Notizen
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