Acetic Anhydride → HCID 54047966, compound

Participants

Reaction Steps

The [4-(trialkylsilylalkylamino)phenyl]alkenoic acids may be prepared by condensation of the appropriate aldehydes or by dehydration of the corresponding substituted-phenyl-hydroxyalkanoic acids. For example, ethyl 5-[4-[14-(trimethylsilyl)tetradecylamino]phenyl]-2,4-pentadienoate is obtained by the Wittig reaction of 4-[14-(trimethylsilyl)tetradecylamino]benzaldehyde with the Wittig reagent, triethyl 4-phosphonocrotonate. Alternatively, these alkenoic acids are obtained by heating 4-[N-trialkylsilylalkyl-N-(methyl or acetyl)amino]benzaldehydes with the sodium salt of the carbanion of ethyl acetate or with a mixture of ethyl acetate, acetic anhydride and potassium acetate. The second method is illustrated by dehydration of ethyl 3-[4-[14-(trimethylsilyl)tetradecylamino]phenyl]-3-hydroxypropionate to yield ethyl 4-[14-(trimethylsilyl)tetradecylamino]cinnamate.

Provenance & Evidence