2-(4,7-Dimethoxy-5-acetylbenzofuran-6-yl)oxymethyl-4-isopropyl-6-methoxysaccharin → 2-(5-Acetyl-4,7-dihydro-4,7-dioxobenzofuran-6-yl)oxymethyl-4-isopropyl-6-methoxysaccharin

HRID 129059

Reaktionsgleichung

Reaktionsgleichung von HRID 129059
[N+]([O-])([O-])=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[NH4+].[NH4+].[NH4+].[NH4+].C[O:30][C:31]1[C:36]2[CH:37]=[CH:38][O:39][C:35]=2[C:34]([O:40]C)=[C:33]([O:42][CH2:43][N:44]2[C:54](=[O:55])[C:53]3[C:48](=[CH:49][C:50]([O:59][CH3:60])=[CH:51][C:52]=3[CH:56]([CH3:58])[CH3:57])[S:45]2(=[O:47])=[O:46])[C:32]=1[C:61](=[O:63])[CH3:62]>O.C(#N)C>[C:61]([C:32]1[C:31](=[O:30])[C:36]2[CH:37]=[CH:38][O:39][C:35]=2[C:34](=[O:40])[C:33]=1[O:42][CH2:43][N:44]1[C:54](=[O:55])[C:53]2[C:48](=[CH:49][C:50]([O:59][CH3:60])=[CH:51][C:52]=2[CH:56]([CH3:58])[CH3:57])[S:45]1(=[O:47])=[O:46])(=[O:63])[CH3:62]

Komponenten

5

Edukt 2

HCID 700458652-(4,7-Dimethoxy-5-acetylbenzofuran-6-yl)oxymethyl-4-isopropyl-6-methoxysaccharinHCID 86748360Tetraammonium hexanitrate

Produkt 1

HCID 152931502-(5-Acetyl-4,7-dihydro-4,7-dioxobenzofuran-6-yl)oxymethyl-4-isopropyl-6-methoxysaccharinAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of triceric tetraammonium hexanitrate (0.98 g) in water (3 mL) was added dropwise to a solution of 2-(4,7-dimethoxy-5-acetylbenzofuran-6-yl)oxymethyl-4-isopropyl-6-methoxysaccharin (0.3 g) in acetonitrile (5 mL). The mixture was stirred at room temperature for 15 minutes and poured into ice-water. The resulting gold colored solid was purified by rapid chromatography on silica gel with dichloromethane-ether (95:5) as eluant and crystallization with sonication from ethanol affording 2-(5-acetyl-4,7-dihydro-4,7-dioxobenzofuran-6-yl)oxymethyl-4-isopropyl-6-methoxysaccharin (0.13 g, 46.6% yield, m.r. 193°-195° C. with decomposition).

Aufarbeitung

  1. customThe resulting gold colored solid was purified by rapid chromatography on silica gel with dichloromethane-ether (95:5) as eluant
  2. customcrystallization
  3. customwith sonication from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-eb8f21e5d24d4f658eadd4fd625ea9cb
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466701

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