Ethyl bromopyruvate → Ethyl 2-(pentan-3-yl)thiazole-4-carboxylate

HRID 1689380

Reaktionsgleichung

Reaktionsgleichung von HRID 1689380
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:10]([CH:12]([CH2:16][CH3:17])[C:13](=[S:15])[NH2:14])[CH3:11]>C(O)C>[CH3:11][CH2:10][CH:12]([C:13]1[S:15][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:14]=1)[CH2:16][CH3:17]

Komponenten

4

Edukt 2

HCID 66144Ethyl bromopyruvateHCID 3062527Butyramide, 2-ethylthio-

Produkt 1

HCID 57989261Ethyl 2-(pentan-3-yl)thiazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl 3-bromo-2-oxopropanoate (2.5 mL) was added dropwise to a solution of 2-ethylbutanethioamide (example 71, step b) (3.8 g) in ethanol (100 mL) and the resulting mixture heated at reflux overnight. The solvent was evaporated and the residue partitioned between ethyl acetate (100 mL) and saturated sodium hydrogen carbonate solution (100 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (2×100 mL). The combined organic solutions were washed with brine (100 mL), dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with 20:1 isohexane:ethyl acetate. The fractions containing product were combined and evaporated to give the subtitled compound as a yellow oil. Yield 2.8 g.

Aufarbeitung

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated
  4. customthe residue partitioned between ethyl acetate (100 mL) and saturated sodium hydrogen carbonate solution (100 mL)
  5. customThe layers were separated
  6. extractionthe aqueous phase extracted with ethyl acetate (2×100 mL)
  7. washThe combined organic solutions were washed with brine (100 mL)
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by silica gel chromatography
  12. washeluting with 20:1 isohexane
  13. additionThe fractions containing product
  14. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-77d76650d1944039938a54281b1295a6
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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