Reacción #2348128

Ecuación de reacción

H2O

3-amino-4-[(E)-2-(4-hydroxy-phenyl)vinyl]phenol

acetic anhydride

Et3N

→

N-{5-hydroxy-2-[(E)-2-(4-hydroxyphenyl)vinyl]phenyl}-acetamide

Rendimiento 46.4%

Disolventes

methanol

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture was concentrated by vacuum evaporation
2. 2
   Otrowas not further purified
3. 3
   OtroThe crude mixture from the previous reaction
4. 4
   workup.STIRRINGThe resulting solution was vigorously stirred at rt for 1 h
5. 5
   OtroAll volatile solvents were evaporated

Procedimiento

To the solution of 3-amino-4-[(E)-2-(4-hydroxy-phenyl)vinyl]phenol (100 mg) in anhydrous THF was added 225 mg of acetic anhydride and 223 mg of Et3N. The resulting solution was stirred at rt overnight. The reaction mixture was concentrated by vacuum evaporation. The residue, which was identified as mainly desired compound by 1H-NMR, was not further purified and used directly for the next step. The crude mixture from the previous reaction was dissolved in 30 mL of methanol. K2Co3 (197 mg, ˜12 eq.) was added as well as 20 mL of H2O. The resulting solution was vigorously stirred at rt for 1 h. All volatile solvents were evaporated and the residue was loaded on a silica gel column with 5% MeOH/dichloromethane as eluent to give N-{5-hydroxy-2-[(E)-2-(4-hydroxyphenyl)vinyl]phenyl}-acetamide (55 mg, 46.4% in two steps). MS (ES) m/z: 270.14 (M+1); Mp. 227-229° C.

Fuente