Diethyl P-((4-methylphenyl)methyl)phosphonate → HCID 54379836, Verbindung

HRID 414579

Reaktionsgleichung

Reaktionsgleichung von HRID 414579
[CH:1]([C:3]1[S:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)=O.[CH3:14][C:15]1[CH:29]=[CH:28][C:18]([CH2:19]P(=O)(OCC)OCC)=[CH:17][CH:16]=1.C[O-].[Na+]>CN(C)C=O>[CH3:14][C:15]1[CH:29]=[CH:28][C:18]([CH:19]=[CH:1][C:3]2[S:4][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 3050Diethyl P-((4-methylphenyl)methyl)phosphonateHCID 1770535-Phenylthiophene-2-carbaldehydeHCID 10942334Sodium Methoxide

Produkt 1

HCID 54379836HCID 54379836, VerbindungAusbeute 49,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 1.52 gram (0.008 mole) of 2-formyl-5-phenylthiophene and 2.0 grams (0.00820 mole) of diethyl 4-methylbenzylphosphonate in 40 mL of N,N-dimethylformamide was added 0.53 gram (0.0098 mole) of sodium methoxide. The reaction mixture was stirred at room temperature for approximately 18 hours and then was quenched with 50 mL of an aqueous solution saturated with ammonium chloride. A precipitate formed and was collected by filtration. The filter cake was washed with water. The washed solid was purified by column chromatography on silica gel, eluting with chloroform:n-hexane (10:90) yielded 1.1 gram of 2-(4-methylphenyl)-1-(5-phenylthien-2-yl)ethene as a solid, m.p. 159°-160° C.

Aufarbeitung

  1. customwas quenched with 50 mL of an aqueous solution saturated with ammonium chloride
  2. customA precipitate formed
  3. filtrationwas collected by filtration
  4. washThe filter cake was washed with water
  5. customThe washed solid was purified by column chromatography on silica gel
  6. washeluting with chloroform:n-hexane (10:90)

Quellen und Nachweise

ORD-Eintrag
ord-382f0be6e0c5411ea1930300a25ddc48
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04792567

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