Magnesium Chloride → Methyl (4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)acetate

HRID 17584

Reaktionsgleichung

Reaktionsgleichung von HRID 17584
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([CH:12]3[CH2:14][CH2:13]3)[O:11][C:7]=2[C:6]([CH:15](C(OC)=O)[C:16]([O:18][CH3:19])=[O:17])=[C:5]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:4]=1[CH3:30])#[N:2].[Cl-].[Mg+2].[Cl-]>CS(C)=O.O>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([CH:12]3[CH2:14][CH2:13]3)[O:11][C:7]=2[C:6]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:5]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:4]=1[CH3:30])#[N:2]

Komponenten

5

Edukt 2

HCID 5360315Magnesium ChlorideHCID 86630880Dimethyl 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)malonate

Produkt 1

HCID 86630881Methyl (4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)acetateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Dimethyl 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)malonate (I-294) (2.887 g, 7.11 mmol) was dissolved in dimethyl sulfoxide (50 ml) and water (5 ml), then at room temperature, magnesium chloride (2.03 g, 21.34 mmol) was added. The solution was stirred at 90° C. for 23 hours, then cooled to room temperature. The solvent was evaporated away under reduced pressure, the residue was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and 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 (2.216 g, 90%) as a pale yellow solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-b74b11804c1f4443a72cecc559d303fe
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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