Potassium Carbonate → HCID 53762825, compound

Participants

Reaction Steps

A mixture of 120 mg (0.88 mmole) of 6-methyl-5-octen-7-yn-2-one (produced in accordance with Example II), 2.00 mL (19 mmoles, the excess of which can be quantitatively recovered by distillation at reduced pressure after the reaction is complete) of 3-chloro-2-chloromethyl-1-propene (purchased from Aldrich Chemical Co., Milwaukee, Wis.), 193 mg (1.4 mmoles) of anhydrous potassium carbonate, 20 mg (0.20 mmole) of cuprous chloride, and 20 mg (0.087 mmole) of benzyltriethylammonium chloride in 2.00 mL of acetonitrile (HPLC-grade, purchased from Aldrich Chemical Co., Milwaukee, Wis.) was stirred vigorously at room temperature for 22 hours, during which time the mixture was maintained under an atmosphere of nitrogen. The mixture was then diluted with 40 mL of 1:1 (v/v) ether:hexane and filtered through a small pad of Hyflo Super-Cel® filtering aid. The filtrate was washed with 20 mL of 5% aqueous sodium chloride, then dried over anhydrous magnesium sulfate, and re-filtered. Removal of the volatile organic material by evaporation at reduced pressure (50 mm) and recovery of unreacted 3-chloro-2-chloromethyl-1-propene by evaporative fractional distillation at reduced pressure (2.5 mm) afforded 146 mg (74% yield) of the named ketone after distillation in the presence of a small amount of calcium carbonate: boiling point 122°-130° C. (bath temperature, 0.20 mm). Proton NMR analysis indicated the presence of a minor impurity, subsequently found to have been present as a contaminant in 3-chloro-2-chloromethyl-1-propene. The named ketone was characterized by a singlet at δ1.78 (CH3 bonded to C-6), a singlet at δ2.12 (CH3C=O), a singlet at δ3.15 (2 hydrogens bonded to C-9), and a singlet at δ4.05 (CH2Cl).

Provenance & Evidence