Dimethyl malonate → Dimethyl 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)malonate

HRID 17583

Reaktionsgleichung

Reaktionsgleichung von HRID 17583
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:21]#[N:22])[C:10]([CH3:20])=[C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:12]=3F)[N:8]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:29]([O:36][CH3:37])(=[O:35])[CH2:30][C:31]([O:33][CH3:34])=[O:32].C(OCC)(=O)C>CS(C)=O.O>[C:21]([C:9]1[C:7]2[N:8]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[O:5][C:6]=2[C:12]([CH:30]([C:29]([O:36][CH3:37])=[O:35])[C:31]([O:33][CH3:34])=[O:32])=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]=1[CH3:20])#[N:22]

Komponenten

7

Edukt 4

HCID 7943Dimethyl malonateHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 510414282-Cyclopropyl-7-fluoro-5-methyl-6-phenylbenzoxazole-4-carbonitrile

Produkt 1

HCID 86630880Dimethyl 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)malonateAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-Cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-173) (2.69 g, 9.20 mmol) was dissolved in dimethyl sulfoxide (50 ml), then at room temperature, potassium carbonate (3.82 g, 27.61 mmol) and dimethyl malonate (2.1 ml, 18.41 mmol) were added. The solution was stirred under nitrogen atmosphere at 90° C. for 14 hours. The reaction liquid was cooled to room temperature, then ethyl acetate and water were added to the reaction liquid, followed by vigorously stirring for 10 minutes. The aqueous layer was separated, extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=3:1, v/v) to obtain the entitled compound (2.878 g, 77%) as a colorless gel

Aufarbeitung

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. stirringby vigorously stirring for 10 minutes
  4. customThe aqueous layer was separated
  5. extractionextracted twice with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe insoluble matter was separated by filtration
  9. customthe solvent was evaporated away
  10. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-1a67ffd2cb4b413280569e617930fcf0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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