Diethyl Ether → Oct-5-en-7-yn-2-one

Participants

Reaction Steps

In accordance with a procedure suggested by L. Miginiac, et al., Org. Prep. Proced. Int., 10, 261 (1978), a mixture containing 2.81 g (17.7 mmoles) of 5-bromo-3-methyl-3-penten-1-yne (produced in accordance with Example I), 3.27 g (23.6 mmoles) of anhydrous potassium carbonate, and 2.00 mL (19.5 mmoles) of 2,4-pentanedione (purchased from Aldrich Chemical Co., Milwaukee, Wis.) in 12.0 mL of absolute ethanol was heated, protected from atmospheric moisture, at reflux for 19 hours. The cooled mixture was diluted with 60 mL of water to dissolve the inorganic solids and the product was isolated by extraction (3×60 mL) with 1:1 (v/v) ether:hexane. After subsequent washing of the combined organic extracts with 10% aqueous sodium chloride (3×80 mL), the organic layer was dried over anhydrous magnesium sulfate and filtered. Removal of the volatile organic solvents by evaporation at reduced pressure, followed by evaporative distillation, afforded 1.67 g (69% yield) of the named ketone: boiling point 82°-91° C. (bath temperature, 2.5 mm). The identity and purity of this known ketone were ascertained by IR and proton NMR analysis. An alternate synthesis of this ketone has been described by P. I. Zakharova, et al., Chem. Abstracts. 75, 109784h (1971).

Provenance & Evidence