4-Hydroxybenzaldehyde → HCID 20225450, Verbindung

Reaktionsgleichung

[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8]OS(C1C=CC(C)=CC=1)(=O)=O)[CH:2]=[CH2:3].[OH:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1.[OH-].[K+]>C(O)C>[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1)[CH:2]=[CH2:3]

Komponenten

Versuchsvorschrift

4-allyloxybutyl-p-toluene sulfonate is reacted with p-hydroxybenzaldehyde in the presence of KOH and C2H5OH to form 4-(4-allyloxybutoxy)benzaldehyde which is reacted with malonic acid in the presence of pyridine to form p-(4-allyloxybutoxy)cinnamic acid. The acid is esterified with CH3OH and sulfuric acid to yield the methylester, namely methyl p-(4-allyloxybutoxy)cinnamic carboxylate. This methyl ester is then reacted with TosMIC in Et2O/DMSO in the presence of sodium hydride or other strong base to form the substituted pyrrole, represented as follows: ##STR7##