4-(2-(Diethylamino)-Ethoxy)-Benzaldehyde → 2-[4-(2-Diethylamino-ethoxy)-benzylidene]-6-(2-imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

HRID 368304

Reaktionsgleichung

Reaktionsgleichung von HRID 368304
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:20]([N:22]([CH2:25][CH2:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)[CH2:23][CH3:24])[CH3:21]>[OH-].[K+].[Cl-].[Na+].O>[CH2:23]([N:22]([CH2:20][CH3:21])[CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([CH:32]=[C:14]2[CH2:13][CH2:12][C:11]3[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:7][CH2:6][N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)[CH:10]=3)[C:15]2=[O:19])=[CH:34][CH:35]=1)[CH3:24]

Komponenten

5

Edukt 2

HCID 4116744-(2-(Diethylamino)-Ethoxy)-BenzaldehydeHCID 15486912HCID 15486912, Verbindung

Produkt 1

HCID 540331082-[4-(2-Diethylamino-ethoxy)-benzylidene]-6-(2-imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-oneAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14797Potassium HydroxideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

6-(2-Imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (0.505 g, 1.97 mmol) was reacted with 4-(diethylamino)ethoxy benzaldehyde (0.662 g, 3.0 mmol) in 2.5 mL of 4% KOH for 20 hours at room temperature. The reaction was diluted with brine, and the resulting mixture was extracted into DCM. The combined extracts were dried, filtered, and evaporated to dryness. The resulting oil was purified twice by flash chromatography (silica gel, 150 g, 10% MeOH in DCM) to afford 0.274 g (30%) of the title compound as a yellow oil: CI-MS m/e 459 (M+), 460 (M+ +1);

Aufarbeitung

  1. extractionthe resulting mixture was extracted into DCM
  2. customThe combined extracts were dried
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe resulting oil was purified twice by flash chromatography (silica gel, 150 g, 10% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-db5104faed6a4b46a3ecd9f03c9c899e
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133303

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