4-Methylthiazole → 2-Acetyl-4-methylthiazole

HRID 1178198Notes

Reaction equation

HRID 1178198 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 53247972-Acetyl-4-methylthiazoleYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fbe8899a89ce4e0381341edcbacf41d6
Source dataset
uspto-grants-2007_10
Patent number
US07276502B2

Reaction notes

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