Water → Diallyl {2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}{2-[4-(methoxycarbonyl)phenyl]ethyl}-malonate

HRID 1920575Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1920575
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH:15]([C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17])=[CH:9][CH:8]=1)=[O:6].Br[CH2:29][CH2:30][C:31]1([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:33][CH2:32]1.O>CN(C=O)C.C(OCC)(=O)C>[CH2:38]([O:37][C:35](=[O:36])[CH2:34][C:31]1([CH2:30][CH2:29][C:15]([CH2:14][CH2:13][C:10]2[CH:9]=[CH:8][C:7]([C:5]([O:4][CH3:3])=[O:6])=[CH:12][CH:11]=2)([C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17])[CH2:32][CH2:33]1)[CH3:39]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 57965762Diallyl 2-[4-(methoxycarbonyl)phenyl]ethylmalonateHCID 57965767Ethyl [1-(2-bromoethyl)cyclopropyl]acetate

Produkt 1

HCID 57965761Diallyl {2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}{2-[4-(methoxycarbonyl)phenyl]ethyl}-malonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Under argon and at 0° C., 0.22 g (5.41 mmol) of sodium hydride (60% strength dispersion in mineral oil) is added a little at a time to a solution of 1.34 g (3.87 mmol) of diallyl 2-[4-(methoxy-carbonyl)phenyl]ethylmalonate in 10 ml of anhydrous DMF. The mixture is stirred at 40° C. for 30 min, and a solution of 1.00 g (4.25 mmol) of ethyl [1-(2-bromoethyl)cyclopropyl]acetate in 5 ml of anhydrous DMF is then added dropwise at this temperature. The reaction mixture is then heated at 110° C. for 12 hours. After addition of 100 ml of water and 100 ml of ethyl acetate and phase separation, the aqueous phase is extracted with ethyl acetate. The organic phase is then washed five times with water and once with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The crude product is purified by preparative HPLC. This gives 0.33 g (17% of theory) of the title compound as a colorless oil.

Aufarbeitung

  1. temperatureThe reaction mixture is then heated at 110° C. for 12 hours
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. washThe organic phase is then washed five times with water
  4. dry with materialonce with saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  5. customThe crude product is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cb66d4553fb146b4bc3ef5e0e6bdaa27
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168821B2

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