Water → 3-[5-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-yl]acrylonitrile

HRID 85290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 85290
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH2:14]([N:18]([CH2:36][CH2:37][CH2:38][CH3:39])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[CH:26][C:27]2[S:31][C:30]([CH:32]=O)=[CH:29][CH:28]=2)=[C:21]([O:34][CH3:35])[CH:20]=1)[CH2:15][CH2:16][CH3:17].O>O1CCCC1>[CH2:14]([N:18]([CH2:36][CH2:37][CH2:38][CH3:39])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[CH:26][C:27]2[S:31][C:30]([CH:32]=[CH:5][C:3]#[N:4])=[CH:29][CH:28]=2)=[C:21]([O:34][CH3:35])[CH:20]=1)[CH2:15][CH2:16][CH3:17]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 866675385-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-carboaldehyde

Produkt 1

HCID 680092803-[5-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-yl]acrylonitrileAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 111 mg (4.63 mmol) of sodium hydride, 8 ml of tetrahydrofuran was added. To this mixture, 820 mg (4.63 mmol) of diethyl cyanomethylphosphonate was added dropwise under ice cooling, and the mixture was stirred for 30 minutes. Next, 860 mg (2.31 mmol) of 5-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-carboaldehyde in tetrahydrofuran was added dropwise, and the mixture was stirred for 1 hour. The reaction mixture was poured into water and subjected to extraction with ethyl acetate. The extract was washed with a saturated saline solution, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give 828 mg of a deep red oily matter (yield: 90.7%).

Aufarbeitung

  1. stirringthe mixture was stirred for 1 hour
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe extract was washed with a saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. customto give 828 mg of a deep red oily matter (yield: 90.7%)

Quellen und Nachweise

ORD-Eintrag
ord-f71b300b87df400391f69adfa468627c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846955B2

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