Reacción #1340624

Ecuación de reacción

benzylamine dihydrochloride

diisopropylethylamine

dimethyl 3-oxopentanedioate

→

methyl (1-benzyl-5-hydroxy-1H-pyrazol-3-yl)acetate

Rendimiento 64.2%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe resulting mixture was heated
2. 2
   Temperaturaat reflux for 18 h
3. 3
   Concentraciónbefore being concentrated in vacuo
4. 4
   OtroThe resulting brown oil was purified by flash chromatography over SiO2 (CH2Cl2:MeOH, 97:3)

Procedimiento

To a suspension of benzylamine dihydrochloride (1.000 g, 5.126 mmol, 1 equiv.) in anhydrous toluene (25 ml) were added successively diisopropylethylamine (1.32 ml, 10.252 mmol, 2 equiv.) and dimethyl 3-oxopentanedioate (0.893 g, 5.126 mmol, 1 equiv.). The resulting mixture was heated at reflux for 18 h before being concentrated in vacuo. The resulting brown oil was purified by flash chromatography over SiO2 (CH2Cl2:MeOH, 97:3). 0.810 g of pure methyl (1-benzyl-5-hydroxy-1H-pyrazol-3-yl)acetate was obtained as a white solid. Yield 64%. MS (ESI+): 247.1; MS (ESI−): 245.1.

Fuente