Dimethylformamide → HCID 53433946, Verbindung

HRID 388472

Reaktionsgleichung

Reaktionsgleichung von HRID 388472
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=[C:8]([CH3:11])[CH:9]=2)[CH:4]=[CH:3]1.P(Cl)(Cl)(OP(Cl)(Cl)=O)=O.CN([CH:25]=[O:26])C>>[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=[C:8]([CH3:11])[CH:9]=2)[C:4]([CH:25]=[O:26])=[CH:3]1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 4432411Diphosphoryl tetrachlorideHCID 13411053HCID 13411053, Verbindung

Produkt 1

HCID 53433946HCID 53433946, VerbindungAusbeute 93 %

Versuchsvorschrift

A solution of 1,4,6-trimethyl-1H-indole (800 mg, 5 mmol) in DMF (0.9 mL) is cooled to 5° C. under nitrogen. Pyrophosphoryl chloride (1.4 mL, 10 mmol) is then slowly introduced. Upon complete addition the cooling bath is removed and the reaction is allowed to warm to ambient temperature. After a total of 45 minutes, the reaction is recooled to 5° C. and is slowly quenched with 2N NaOH. The pH of the solution is adjusted to 8. The precipitated solid is collected by filtration and is washed with water to afford 1,4,6-Trimethyl-1H-indole-3-carbaldehyde (875 mg, 93%).

Aufarbeitung

  1. additionUpon complete addition the cooling bath
  2. customis removed
  3. customAfter a total of 45 minutes
  4. customis recooled to 5° C.
  5. customis slowly quenched with 2N NaOH
  6. filtrationThe precipitated solid is collected by filtration
  7. washis washed with water

Quellen und Nachweise

ORD-Eintrag
ord-9b2fc06614244885b6f6f2cb541a336c
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377949B2

Verknüpfte Notizen

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