Reacción #544028

Ecuación de reacción

NaOH

methyl 4-({[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}methyl)benzoate

→

title compound

Rendimiento 99.0%

4-({[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}methyl)benzoic acid

Rendimiento 99.0%

Disolventes

THF

methanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed under nitrogen for 7 h
2. 2
   FiltraciónThe reaction was filtered
3. 3
   workup.ADDITIONacidified by the addition of 2.5 mL of 1 N HCl
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   Otroto remove the THF and methanol
6. 6
   FiltraciónThe solid present was collected by filtration
7. 7
   Lavadorinsed with water
8. 8
   Otrodried under reduced pressure

Procedimiento

A mixture of methyl 4-({[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}methyl)benzoate (235 mg, 0.461 mmol), prepared in the previous step, and 1 N NaOH (692 μL, 0.692 mmol) in 30 mL of THF plus 30 mL of methanol plus 5 mL of water was refluxed under nitrogen for 7 h. The reaction was filtered, cooled to room temperature, acidified by the addition of 2.5 mL of 1 N HCl and then concentrated under reduced pressure to remove the THF and methanol. The solid present was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (225 mg, 99%) as a white solid, mp 309–310° C. Elemental Analysis for C34H25NO3.0.05 C4H8O.0.19 H2O Calc'd: C, 81.73; H, 5.17; N, 2.79. Found: C, 81.94; H, 5.02; N, 2.65.

Fuente