Water → HCID 22618744, Verbindung

HRID 617609

Reaktionsgleichung

Reaktionsgleichung von HRID 617609
[CH2:1]([CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[H-].[Na+].[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31]I)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C)C=O.O1CCCC1>[CH2:1]([C:3]([CH2:31][CH2:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:25][CH:26]=1)([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8610Diethyl ethylmalonateHCID 24758Sodium hydrideHCID 104272231-((4-(2-Iodoethyl)phenoxy)methyl)benzene

Produkt 1

HCID 22618744HCID 22618744, VerbindungAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diethyl ethylmalonate (50 g) was added to a suspension of sodium hydride (11 g) in dimethylformamide (200 ml) and tetrahydrofuran (50 ml), at 0° C., and the mixture was stirred at room temperature for 35 minutes. A solution of 2-(4-benzyloxyphenyl)ethyl iodide (90 g) was added to the reaction mixture at 0° C. and the whole mixture was stirred at 0° C. for 20 minutes and allowed to stand at room temperature overnight. The resultant mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and a saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure and the residue obtained was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:9) to give the subject compound (100 g).

Aufarbeitung

  1. stirringthe whole mixture was stirred at 0° C. for 20 minutes
  2. waitto stand at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materiala saturated brine and dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe residue obtained
  8. customwas purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:9)

Quellen und Nachweise

ORD-Eintrag
ord-7b33fc8433744a6985b09c3543fec6e1
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05948820

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