C-Alkylation of the acetoacetate anions and of sodium naphthoxide is highly favoured on alumina, while O-alkylation of the acetoacetate anion predominates in tetrahydrofuran in the presence of solid hexamethylphosphoric triamide.
G. Bram, N. Geraghty, G. Nee and J. Seyden-Penne, J. Chem. Soc., Chem. Commun., 1980, 325 DOI: 10.1039/C39800000325
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