Arens-van Dorp Synthesis; Isler Modification

D. A. van Dorp, J. F. Arens, Nature 160, 189 (1947); J. F. Arens et al., Rec. Trav. Chim. 68, 604, 609 (1949); O. Isler et al., Helv. Chim. Acta 39, 259 (1956).

The preparation of alkoxyethynyl alcohols from ketones and ethoxyacetylene. In the Isler modification the tedious preparation of ethoxyacetylene is obviated by treating β-chlorovinyl ether with lithium amide to yield lithium ethoxyacetylene, which is then condensed with the ketone:

H. Heusser et al., Helv. Chim. Acta 33, 370 (1950); J. F. Arens, Advan. Org. Chem. 2, 117-212 (1960); H. Meerwein, Houben-Weyl 6/3, 189 (1965). Cf. Favorskii-Babayan Synthesis; Nef Synthesis.