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Chloral → 1-Methyl-alpha-trichloromethylpyrrole-2-methanol

HRID 1732560
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1732560
[OH-].[K+].[O:3]=[CH:4][C:5]([Cl:8])([Cl:7])[Cl:6].C([C:11]1[N:15]([CH3:16])[C:14](CC(OC)=O)=[CH:13][CH:12]=1)#N>O>[CH3:16][N:15]1[CH:11]=[CH:12][CH:13]=[C:14]1[CH:4]([OH:3])[C:5]([Cl:8])([Cl:7])[Cl:6]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6407ChloralHCID 14797Potassium HydroxideHCID 2386959Methyl 2-(5-cyano-1-methyl-1H-pyrrol-2-yl)acetate

Produkt 1

HCID 155715331-Methyl-alpha-trichloromethylpyrrole-2-methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

1-Methyl-2-(2',2',2'-trichloro-1'-hydroxyethyl)pyrrole (1.14 g, 5 mmol), which was prepared by the procedure of Example 2, was dissolved in the solvent (15 ml) shown in the next table. After water (15 ml) and alkali metal cyanide (MCN: amount is shown in the table) were added to the solution, a solution of potassium hydroxide in water (10 ml) was added during a period of 6 hours under vigorous stirring at 45° C. After confirmation of the disappearance of starting chloral adduct (overnight), the reaction mixture was diluted with water (100 ml) and extracted twice with ethyl acetate. The combined organic extracts were washed with brine and dried over anhydrous magnesium sulfate. Most of the solvent was removed under reduced pressure and the residue was dissolved again in the 50 ml exact amount of ethyl acetate. A portion of the solution was taken up and treated with diazomethane dissolved in ether. After removal of the excess diazomethane under reduced pressure, trans-stilbene was added as the internal standard and the yield of methyl 5-cyano-1-methylpyrrole-2-acetate (theoretical yield; 5 mmol) was determined by GC (2% EGA column, 1 m, 160° C.).

Aufarbeitung

  1. additionwere added to the solution
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customMost of the solvent was removed under reduced pressure
  6. dissolutionthe residue was dissolved again in the 50 ml exact amount of ethyl acetate
  7. additiontreated with diazomethane
  8. dissolutiondissolved in ether
  9. customAfter removal of the excess diazomethane under reduced pressure, trans-stilbene
  10. additionwas added as the internal standard
  11. customwas determined by GC (2% EGA column, 1 m, 160° C.)

Quellen und Nachweise

ORD-Eintrag
ord-fbf426d271fe4d729e6d2a71ffa314ac
Quelldatensatz
uspto-grants-1980_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04238396

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