3-Methyl-2-butanone → 4,5,6-triiodo-2,3,3-trimethyl-3H-indole

HRID 508293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508293
[I:1][C:2]1[CH:3]=[C:4]([NH:10]N)[CH:5]=[C:6]([I:9])[C:7]=1[I:8].[CH3:12][CH:13]([CH3:17])[C:14](=O)[CH3:15]>C(O)(=O)C>[I:1][C:2]1[C:7]([I:8])=[C:6]([I:9])[CH:5]=[C:4]2[C:3]=1[C:13]([CH3:17])([CH3:12])[C:14]([CH3:15])=[N:10]2

Komponenten

4

Edukt 2

HCID 112513-Methyl-2-butanoneHCID 866953333,4,5-Triiodophenylhydrazine

Produkt 1

HCID 717360084,5,6-triiodo-2,3,3-trimethyl-3H-indoleAusbeute 27,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

2 g of 3,4,5-triiodophenylhydrazine, and 0.86 g (10 mmol) of 3-methyl-2-butanone were refluxed in 15 mL of acetic acid for 16 hours. The acetic acid was evaporated, the residue was dissolved in chloroform, washed with aqueous solutions of NaHCO3, followed by Na2S2O3 and water. The organic layer was dried and chloroform was removed under reduced pressure by a rotary evaporator. The residue was column purified (Silica gel 60, 0-2% methanol-chloroform) to give 0.6 g of 4,5,6-triiodo-2,3,3-trimethyl-3H-indole. 1H-NMR (200 MHz, DMSO-d6), δ, ppm: 8.04 (1H, s, arom.), 2.19 (3H, s, 2-CH3), 1.30 (6H, s, C(CH3)2).

Aufarbeitung

  1. customThe acetic acid was evaporated
  2. dissolutionthe residue was dissolved in chloroform
  3. washwashed with aqueous solutions of NaHCO3
  4. customThe organic layer was dried
  5. customchloroform was removed under reduced pressure by a rotary evaporator
  6. custompurified (Silica gel 60, 0-2% methanol-chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-c8f6c027dbf84cdbb665f7d3bde2b94e
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09095612B2

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