Cesium carbonate → HCID 10670907, Verbindung

HRID 129056

Reaktionsgleichung

Reaktionsgleichung von HRID 129056
C(=O)([O-])[O-:2].[Cs+].[Cs+].[C:7]1([C:13]2[C:14](=[O:18])[O:15][CH2:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[CH2:20][N:21]1[C:31](=[O:32])[C:30]2[C:25](=[CH:26][C:27]([O:36][CH3:37])=[CH:28][C:29]=2[CH:33]([CH3:35])[CH3:34])[S:22]1(=[O:24])=[O:23]>CO.CN(C)C=O>[O:18]=[C:14]1[C:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[C:17]([O:2][CH2:20][N:21]2[C:31](=[O:32])[C:30]3[C:25](=[CH:26][C:27]([O:36][CH3:37])=[CH:28][C:29]=3[CH:33]([CH3:35])[CH3:34])[S:22]2(=[O:24])=[O:23])[CH2:16][O:15]1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxideHCID 10986536HCID 10986536, Verbindung

Produkt 1

HCID 10670907HCID 10670907, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Cesium carbonate (0.82 g) was added to a solution of 3-phenyl-2(5H)-furanone (0.88 g) in methanol (15 mL) and the mixture was stirred at room temperature for one hour and stripped of methanol. 2-Chloromethyl-4-isopropyl-6-methoxysaccharin (1.52 g) was added to a solution of the residue in dimethylformamide (15 mL) and the mixture was stirred at room temperature for two days. Silica gel (4.4 g) was added, volatiles were removed under vacuum, and the solid was subjected to flash chromatography on silica gel using ethyl acetate-hexane (3:7) as eluant. Recrystallization of the product from ethanol-ether gave 2-(2,5-dihydro-2-oxo-3-phenylfuran-4-yl)oxymethyl-4-isopropyl-6-methoxysaccharin as a colorless solid (0.45 g, 20% yield, m.r. 180°-182° C. ).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for two days
  2. additionSilica gel (4.4 g) was added
  3. customvolatiles were removed under vacuum
  4. customRecrystallization of the product from ethanol-ether

Quellen und Nachweise

ORD-Eintrag
ord-1d56cfefff0e479598e4c94eaf10493d
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466701

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