4-Methylthiazole → 2-Acetyl-4-methylthiazole

HRID 1178198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178198
[Li]CCCC.[CH3:6][C:7]1[N:8]=[CH:9][S:10][CH:11]=1.CON(C)[C:15](=[O:17])[CH3:16]>CCOCC>[CH3:6][C:7]1[N:8]=[C:9]([C:15](=[O:17])[CH3:16])[S:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 127484-MethylthiazoleHCID 537505N-Methoxy-N-methylacetamideHCID 178418339Butyllithium

Produkt 1

HCID 53247972-Acetyl-4-methylthiazoleAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a stirred solution of n-BuLi (2M in pentane; 22.4 mL, 0.045 mol) in 70 mL of dry ether at −78° C. was added dropwise 4-methylthiazole (3.7 g, 0.037 mol) in 30 mL of ether over a period of 30 minutes. The mixture was stirred for 1 h, then N-methoxy-N-methylacetamide (4.37 mL, 0.041 mol) was added dropwise over 10 minutes. After 1 h of stirring at −78° C. the reaction mixture was washed with sat'd NaHCO3 and extracted with ether. The organic layer was dried with Na2SO4 and concentrated in vacuo to give 4.38 g (85%) of 2a as an oil that was used directly for the next step. 1H NMR (CDCl3) δ 7.2 (s, 1H), 2.75 (s, 3H), 2.5 (s, 3H).

Aufarbeitung

  1. stirringAfter 1 h of stirring at −78° C. the reaction mixture
  2. washwas washed with sat'd NaHCO3
  3. extractionextracted with ether
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fbe8899a89ce4e0381341edcbacf41d6
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276502B2

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