Reaktion #2348128

Reaktionsgleichung

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

Ausbeute 46.4%

Lösungsmittel

methanol

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle