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Water → (E)-1-[3-(5-ethyl-4-hydroxy-3-methoxy-1-naphthyl)-1-oxo-2-propenyl]piperidine

HRID 488147
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 488147
[H-].[Na+].C(OP([CH2:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13])(OCC)=O)C.[CH2:20]([C:22]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:23]=1[C:24]([O:36]COC)=[C:25]([O:34][CH3:35])[CH:26]=[C:27]2[CH:32]=O)[CH3:21].O>CN(C)C=O>[CH2:20]([C:22]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:23]=1[C:24]([OH:36])=[C:25]([O:34][CH3:35])[CH:26]=[C:27]2/[CH:32]=[CH:11]/[C:12]([N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)=[O:13])[CH3:21]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 99705695-Ethyl-3-methoxy-4-methoxymethoxy-1-naphthalenecarbaldehydeHCID 13203262Diethyl [2-oxo-2-(piperidin-1-yl)ethyl]phosphonate

Produkt 1

HCID 14986482(E)-1-[3-(5-ethyl-4-hydroxy-3-methoxy-1-naphthyl)-1-oxo-2-propenyl]piperidineAusbeute 111,1 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

0.15 g of 60% sodium hydride was suspended in 20 ml of N,N-dimethylformamide, to which 1.15 g of N-(diethoxyphosphoryl)acetylpiperidine was gradually added at room temperature. After stirring for 10 minutes, a solution of 800 mg of 5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthalenecarbaldehyde in N,N-dimethylformamide (10 ml) was gradually added. After stirring for 20 minutes, water was added, followed by extraction with ethyl acetate. The combined extracts were washed with water and dried over anhydrous magnesium sulfate. After removal of the solvent, the resultant residue was purified by silica gel column chromatography (30% ethyl acetate/hexane) to obtain 1.1 g of the titled compound as pale yellow crystals.

Aufarbeitung

  1. additionwas gradually added at room temperature
  2. stirringAfter stirring for 20 minutes
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removal of the solvent
  7. customthe resultant residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e41e6052f6274f1a9ff49ba561439c8f
Quelldatensatz
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05298649

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