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Trimethylamine → 3-Benzyloxy-2-methyl-1-(2-pivaloyloxyethyl)pyridin-4-one

HRID 374444
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 374444
CN(C)C.[CH2:5]([O:12][C:13]1[C:18](=[O:19])[CH:17]=[CH:16][N:15]([CH2:20][CH2:21][OH:22])[C:14]=1[CH3:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:24](Cl)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26].C(OCC)(=O)C>CN(C)C=O.CO>[CH2:5]([O:12][C:13]1[C:18](=[O:19])[CH:17]=[CH:16][N:15]([CH2:20][CH2:21][O:22][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:14]=1[CH3:23])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 1146TrimethylamineHCID 8857Ethyl AcetateHCID 62493Pivaloyl chloride2×HCID 4046803-Benzyloxy-1-(2-hydroxyethyl)-2-methylpyridin-4-one

Produkt 1

HCID 189971743-Benzyloxy-2-methyl-1-(2-pivaloyloxyethyl)pyridin-4-oneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Trimethylamine (4.7 ml) was added with stirring to a solution of 3-benzyloxy-1-(2-hydroxyethyl)-2-methylpyridin-4-one (2 g) in dimethylformamide (40 ml) and the solution was then heated under reflux while pivaloyl chloride (1 ml) was added dropwise. The mixture was refluxed at 78° C. for two hours whilst monitoring by thin layer chromatography (1:1 v/v ethyl acetate:methanol) when very little change of the mixture was obtained. Further trimethylacetylchloride (3 ml) was therefore added and refluxing continued for another 16 hours. The solution was evaporated to dryness, the resultant solid was dissolved in dichloromethane (100 ml) and this solution was washed with sodium bicarbonate solution (0.05M, 4000 ml) and the organic phase was then dried over anhydrous sodium sulphate, filtered and evaporated to dryness. The resultant crude product was flash chromatographed (silica gel, Kieselgel 60,7754, 20 mm×300 mm column; eluting with acetonitrile:ethyl acetate, 1:9 v/v) to provide the title compound in 60% yield as a colourless solid, m.p. 103°- 105.8° C.

Aufarbeitung

  1. temperaturethe solution was then heated
  2. additionwas added dropwise
  3. customwas obtained
  4. temperaturerefluxing
  5. customThe solution was evaporated to dryness
  6. dissolutionthe resultant solid was dissolved in dichloromethane (100 ml)
  7. washthis solution was washed with sodium bicarbonate solution (0.05M, 4000 ml)
  8. dry with materialthe organic phase was then dried over anhydrous sodium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customchromatographed
  12. wash(silica gel, Kieselgel 60,7754, 20 mm×300 mm column; eluting with acetonitrile:ethyl acetate, 1:9 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-54ea9f39ff47490e87bd1542acb2ca53
Quelldatensatz
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05480894

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