Reacción #1340628

Ecuación de reacción

methyl[1-(2-chlorophenyl)-5-hydroxy-1H-pyrazol-3-yl]acetate

(4-methoxyphenyl)acetyl chloride

→

methyl {1-(2-chlorophenyl)-5-hydroxy-4-[(4-methoxyphenyl)acetyl]-1H-pyrazol-3-yl}acetate

Rendimiento 70.0%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe mixture of the
2. 2
   ConcentraciónThe resulting red solution was concentrated in vacuo
3. 3
   Otroto afford a red syrup that
4. 4
   Otrowas partitioned between ethylacetate and cold 0.1M HCl
5. 5
   LavadoOrganic phases were washed with brine
6. 6
   Secadodried over Na2SO4
7. 7
   OtroEvaporation of solvent

Procedimiento

The mixture of the above obtained methyl[1-(2-chlorophenyl)-5-hydroxy-1H-pyrazol-3-yl]acetate (Compound of Formula (IV), 1 g, 3.76 mmol, 1 eq.), was suspended in dioxane (10 mL) and Ca(OH)2 (0.557 g, 2 equiv.) and (4-methoxyphenyl)acetyl chloride (0.694 g) under nitrogen, was heated at 120° C. for 45-60 minutes. The resulting red solution was concentrated in vacuo to afford a red syrup that was partitioned between ethylacetate and cold 0.1M HCl. Organic phases were washed with brine and dried over Na2SO4. Evaporation of solvent gave methyl {1-(2-chlorophenyl)-5-hydroxy-4-[(4-methoxyphenyl)acetyl]-1H-pyrazol-3-yl}acetate as a pink solid (1.09 g, 70% yield, 89% HPLC purity). MS (ESI+): 415.9; MS (ESI−): 413.8.

Fuente