2-Nitrothiophene-4-carboxaldehyde → HCID 9860933, Verbindung

HRID 1604735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1604735
[N+:1]([C:4]1[S:5][CH:6]=[C:7]([CH:9]=[O:10])[CH:8]=1)([O-:3])=[O:2].[P:11]([O-:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]>CO>[N+:1]([C:4]1[S:5][CH:6]=[C:7]([CH:9]([P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])[OH:10])[CH:8]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 1447302-Nitrothiophene-4-carboxaldehydeHCID 3780918Diethylphosphite

Produkt 1

HCID 9860933HCID 9860933, VerbindungAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution containing 2-nitro-4-thiophenecarboxaldehyde (2.61 g, 16.6 mmol), diethyl phosphite (2.14 mL, 16.6 mmol), and methanol (5 mis) was adsorbed onto excess basic alumina. After 16 hours the product was extracted with methylene chloride, concentrated and purified by column chromatography (silica gel). Elution with methylene chloride-methanol 19:1 gave the product (3.55 g) as an oil. 1H NMR (CDC13): d, 5.05 (dd,1H,PCH), 4.15 (m,4H,CH2), 1.33 (dt,6H,CH3). MS (DCl): 296 (MH+). C9H14NO6PS.

Aufarbeitung

  1. extractionAfter 16 hours the product was extracted with methylene chloride
  2. concentrationconcentrated
  3. custompurified by column chromatography (silica gel)
  4. washElution with methylene chloride-methanol 19:1

Quellen und Nachweise

ORD-Eintrag
ord-779957d2d513477bbaccf3c0fa5ea775
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05994563

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