Trichloroacetyl chloride → 2,2,2-trichloro-1-(5-methyl-1H-pyrrol-2-yl)ethan-1-one

HRID 655765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655765
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][CH:6]=1.[Cl:7][C:8]([Cl:13])([Cl:12])[C:9](Cl)=[O:10].C([O-])([O-])=O.[K+].[K+]>C(OCC)C>[Cl:7][C:8]([Cl:13])([Cl:12])[C:9]([C:4]1[NH:3][C:2]([CH3:1])=[CH:6][CH:5]=1)=[O:10]

Komponenten

5

Edukt 3

HCID 6420Trichloroacetyl chlorideHCID 11430Potassium CarbonateHCID 124892-Methylpyrrole2×

Produkt 1

HCID 17145712,2,2-trichloro-1-(5-methyl-1H-pyrrol-2-yl)ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

2-Methyl-1H-pyrrole (Intermediate 31, 10 g, 0.123 mmol) in anhydrous diethyl ether (30 ml) was added dropwise over 1 h to a stirred solution of trichloroacetyl chloride (29 g, 0.16 mmol) in anhydrous Et2O (100 ml). The mixture was stirred for a further 1 h then K2CO3 (10 g/30 ml) was added slowly through a dropping funnel. The organic phase was dried over Na2SO4 and treated with decolorizing charcoal (3 g) for 30 min at room temperature. The resulting purple solution was concentrated and triturated with n-hexanes to give the title compound as a purple solid. (16.72 g). NMR (CDCl3): 2.36 (s, 3H), 6.04 (dd, 1H), 7.45 (dd, 1H), 10.344 (s, 1H).

Aufarbeitung

  1. dry with materialThe organic phase was dried over Na2SO4
  2. additiontreated with decolorizing charcoal (3 g) for 30 min at room temperature
  3. concentrationThe resulting purple solution was concentrated
  4. customtriturated with n-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-a4b4722cdac5477c85837a45c51facc3
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071605B2

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