Triethylamine → Ethyl 5-methylpyridine-2-carboxylate

HRID 1650339

Reaktionsgleichung

Reaktionsgleichung von HRID 1650339
[CH2:1](N(CC)CC)C.Br[CH:9]([CH2:15]Br)[C:10]([O:12][CH2:13][CH3:14])=[O:11].CN(C)[CH:19]=[CH:20][C:21]([NH2:23])=C>O1CCOCC1>[CH3:19][C:20]1[CH:1]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:23][CH:21]=1

Komponenten

5

Edukt 3

HCID 8471Triethylamine2×HCID 97945Ethyl 2,3-dibromopropionateHCID 867439031-Dimethylamino-1-aza-3-methyl-1,3-butadiene

Produkt 1

HCID 12243769Ethyl 5-methylpyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

6.1 g of triethylamine are added at 0° C. to 13 g of ethyl 2,3-di-bromopropionate in 50 ml of dioxane. The mixture is stirred for 2 hours at room temperature and then a solution of 5.6 g of 1-dimethylamino-1-aza-3-methyl-1,3-butadiene and 6.1 g of triethylamine in 50 ml of dioxane is added dropwise. The reaction mixture is kept for 30 hours at 70° C. and then cooled and concentrated by evaporation. The residue is partitioned between water and ether and the organic phase is washed with brine, dried and concentrated by evaporation. The residue is distilled under reduced pressure, affording 3.2 g of the title compound as an oil with a boiling point of 69°-74° C. (at 0.08 mbar).

Aufarbeitung

  1. waitThe reaction mixture is kept for 30 hours at 70° C.
  2. temperaturecooled
  3. concentrationconcentrated by evaporation
  4. customThe residue is partitioned between water and ether
  5. washthe organic phase is washed with brine
  6. customdried
  7. concentrationconcentrated by evaporation
  8. distillationThe residue is distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9a1d28c43bd94341a7846ecc45555c03
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04923993

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