Reaktion #216241

ord-eb8f21e5d24d4f658eadd4fd625ea9cb

Reaktionsgleichung

O=[N+]([O-])O.O=[N+]([O-])O.O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].[NH4+].[NH4+].[NH4+].[NH4+]
tetraammonium hexanitrate
COc1cc(C(C)C)c2c(c1)S(=O)(=O)N(COc1c(C(C)=O)c(OC)c3ccoc3c1OC)C2=O
2-(4,7-dimethoxy-5-acetylbenzofuran-6-yl)oxymethyl-4-isopropyl-6-methoxysaccharin
→
COc1cc(C(C)C)c2c(c1)S(=O)(=O)N(COC1=C(C(C)=O)C(=O)c3ccoc3C1=O)C2=O
2-(5-acetyl-4,7-dihydro-4,7-dioxobenzofuran-6-yl)oxymethyl-4-isopropyl-6-methoxysaccharin
Ausbeute 46.6%

Edukte

O=[N+]([O-])O.O=[N+]([O-])O.O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].[NH4+].[NH4+].[NH4+].[NH4+]
tetraammonium hexanitrate
COc1cc(C(C)C)c2c(c1)S(=O)(=O)N(COc1c(C(C)=O)c(OC)c3ccoc3c1OC)C2=O
2-(4,7-dimethoxy-5-acetylbenzofuran-6-yl)oxymethyl-4-isopropyl-6-methoxysaccharin
—
ice water

Reagenzien

Keine

Lösungsmittel

O
water
CC#N
acetonitrile

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05466701uspto-grants-1995_11