Triethylamine → 1-Acetyl-3-(benzyloxy)-2-methylpyridin-4(1H)-one

HRID 1871791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1871791
[CH2:1]([O:8][CH:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]=[C:10]1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](Br)(=[O:19])[CH3:18].C(N(CC)CC)C>CC(C)=O>[C:17]([N:11]1[CH:12]=[CH:13][C:14](=[O:15])[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]1[CH3:16])(=[O:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10482Acetyl bromideHCID 693437942-Methyl-3-(phenylmethoxy)-4(3H)-pyridinone

Produkt 1

HCID 186887761-Acetyl-3-(benzyloxy)-2-methylpyridin-4(1H)-oneAusbeute 64,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

3-Benzyloxy-2-methylpyrid-4-one (4 g) is dissolved in dry acetone (100 ml). Acetylbromide (3 g) and triethylamine (2.7 g) are added and the resulting mixture is mechanically stirred overnight. The mixture is then filtered and the filtrate is rotary evaporated to dryness. The residue is dissolved in methylene chloride and washed with dilute hydrochloric acid (pH 3.0), then twice with water, and is dried over Na2SO4 and rotary evaporated to yield a solid residue. Recrystallisation of this residue from an ethylacetate/hexane mixture gives 1-acetyl-3-benzyloxy-2-methylpyrid-4-one as an oil (3.1 g).

Aufarbeitung

  1. filtrationThe mixture is then filtered
  2. customthe filtrate is rotary evaporated to dryness
  3. dissolutionThe residue is dissolved in methylene chloride
  4. washwashed with dilute hydrochloric acid (pH 3.0)
  5. dry with materialtwice with water, and is dried over Na2SO4
  6. customrotary evaporated
  7. customto yield a solid residue
  8. customRecrystallisation of this residue from an ethylacetate/hexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-12960c2799d14dfa87d28418d0651193
Quelldatensatz
uspto-grants-2000_08
Patentnummer
USRE036831

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