Reaktion #462305

Reaktionsgleichung

(R)-2-(4-Nitro-1H-imidazol-1-yl)-octanoic acid

pTsOH

→

(R)-methyl-2-(4-nitro-1H-imidazol-1-yl)-octanoate

Lösungsmittel

ethyl acetate

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was then heated
2. 2
   Temperaturto reflux for 16 hours
3. 3
   TemperaturUpon cooling
4. 4
   Sonstigethe solvent was removed in vacuo
5. 5
   Sonstigeto give an oil that
6. 6
   WaschenThe solution was washed (2×250 mL) with saturated NaHCO3 solution
7. 7
   TrocknenThe organic was then dried (Na2SO4)
8. 8
   Einengenconcentrated in vacuo

Vorschrift

(R)-2-(4-Nitro-1H-imidazol-1-yl)-octanoic acid (16.0 g, 63.0 mmol) was dissolved in 1 L of anhydrous methanol. To this solution was added pTsOH (300 mg). The reaction was then heated to reflux for 16 hours. Upon cooling, the solvent was removed in vacuo, to give an oil that was dissoved in 300 mL of ethyl acetate. The solution was washed (2×250 mL) with saturated NaHCO3 solution. The organic was then dried (Na2SO4) and concentrated in vacuo to provide 13.2g (78%) of (R)-methyl-2-(4-nitro-1H-imidazol-1-yl)-octanoate as an amber oil. Calculated for C12H19N3O4 : C, 53.32; H, 7.11; N, 15.60. Found: C, 53.23; H, 7.05; N, 15.39.

Quelle