Di-t-butoxyacetylene

[66478-63-5] C10H18O2 (MW 170.25) InChI = 1S/C10H18O2/c1-9(2,3)11-7-8-12-10(4,5)6/h1-6H3 InChIKey = PPVDJWLEHWYMCQ-UHFFFAOYSA-N (a synthon for oxocarbons,1 it transfers a protected enediol fragment by cycloaddition) Physical Data: mp 8.5 °C; bp 30 °C/0.05 mmHg; nD25 = 1.4365. Solubility: completely sol hydrocarbons, ethers, chlorinated solvents, and ethyl acetate; insol water. Form Supplied in: pale yellow oil; not commercially available. Analysis of Reagent Purity: IR (CCl4) cm−1: 2972, 2922, 1470, 1450, 1390, 1367, 1301, 1263, 1245, 1150, 825; 1H NMR (CCl4) δ: 1.31 (s, CH3). Preparative Methods: from 1,2-dichloro-1,2-dimethoxyethane2 or from trans-2,3-dichloro-1,4-dioxane.2b,3 This latter procedure has been thoroughly optimized4 and involves six steps, beginning with dioxane. Purification: usual impurities can be removed by column chromatography on neutral alumina using a column refrigerated at 0 °C and eluting with pentane under N2 pressure. Handling, Storage, and Precautions: most conveniently stored as a solid at −20 °C. It slowly decomposes at rt through elimination of 2-methylpropene.5