γ-Acetylenic ketones was written by Colonge, Jean;Gelin, Rene;Gelin, Mme. Rene. And the article was included in Compt. rend. in 1952.Quality Control of Diethyl 2-(prop-2-yn-1-yl)malonate This article mentions the following:
Condensations of HCCCH2OH (I) with the Na derivatives of AcCH2CO2Et (II) and CH2(CO2Et)2 (III) give mono- and dipropargylated derivatives which can be characterized by Cu, Ag, or Hg derivatives I with II gives 52.7% Et α-propargylacetoacetate (IV), b20 115-120°, d420 1.0325, nD20 1.4515, and 6% Et α,α-dipropargylacetoacetate (V), b20 135°, d420 1.031, nD20 1.4625. Hydrolysis of IV with Na8CO8 solution gave 80% 5-hexyn-2-one (VI), b. 149°, d420 0.9065, nD20 1.4366. Similar hydrolysis of V gave 45% 3-propargyl-5-hexyne-2-one, b. 185°, d420 0.932, nD20 1.4549 (semicarbazone, m. 151°). Ethylation of IV or propargylation of AcCHEt-CO2Et gave similar mixtures: 36% Et α-ethyl-α-propargylacetoacetate (VII), b22 112°, d420 0.9934, nD20 1.4445, and 28% Et 2-ethyl-4-pentynoate. Hydrolysis of VII gave 81% 3-ethyl-5-hexyn-2-one, b. 172-5°, d420 0.897, nD20 1.4372 (semicarbazone, m. 124°). I with III gave 50% Et propargylmalonate, b22 129°, d420 1.0466, nD20 1.4395. VI with NaNH2 in Et2O gave a viscous nondistillable polymer, but no cyclization to HOCMe.CC.CH2.CH2 was noted. In the experiment, the researchers used many compounds, for example, Diethyl 2-(prop-2-yn-1-yl)malonate (cas: 17920-23-9Quality Control of Diethyl 2-(prop-2-yn-1-yl)malonate).
Diethyl 2-(prop-2-yn-1-yl)malonate (cas: 17920-23-9) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Quality Control of Diethyl 2-(prop-2-yn-1-yl)malonate
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics