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Ethyl Acetate → Diethyl (7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine-4-yl)methylenemalonate

HRID 846331
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 846331
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([NH:9][CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]=1[O:22][CH2:23][CH:24](OS(C1C=CC(C)=CC=1)(=O)=O)[CH3:25].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.C(OCC)(=O)C>CN(C)C=O.O>[F:8][C:7]1[CH:6]=[CH:5][C:4]2[N:9]([CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:24]([CH3:25])[CH2:23][O:22][C:3]=2[C:2]=1[F:1]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 146971842,3-Difluoro-6-(2,2-diethoxycarbonylethenyl)amino-[(2-p-toluenesulfonyloxypropyl)oxy]benzene

Produkt 1

HCID 13364401Diethyl (7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine-4-yl)methylenemalonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 791 mg of the compound obtained in Example 4 in 5 ml of anhydrous N,N-dimethylformamide (hereinafter abbreviated as DMF), 207 mg of potassium carbonate and a catalytic amount of 18-crown-6-ether were added, and the mixture was heated at 80° C. for 8.5 hours. To the mixture were added ethyl acetate and water. The mixture was shaken, and the organic layer was separated. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography to yield the titled compound as crystals in quantitative yield. The physical data of the product were identical to those of the authentic specimen as described in Reference Example B-1.

Aufarbeitung

  1. customthe organic layer was separated
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4deaa49bbb644a0d9eea7ef8ddafc305
Quelldatensatz
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05136059

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