Potassium Carbonate → HCID 54074476, compound

Participants

Reaction Steps

The coupling reaction was conducted in the manner described in the procedure of Example XVIII using the following reagents: 162 mg (1.02 mmoles) of a mixture of 2-chloromethyl-6-methyl-1,5-heptadiene and 1-chloro-2,6-dimethyl-2,5-heptadiene (produced in accordance with Example XXI), 138 mg (1.01 mmoles) of 6-methyl-5-octen-7-yn-2-one (produced in accordance with Example II), 232 mg (1.68 mmoles) of anhydrous potassium carbonate, 9 mg (0.09 mmole) of cuprous chloride, and 20 mg (0.088 mmole) of benzyltriethylammonium chloride in 1.00 mL of acetonitrile (HPLC-grade). Isolation of the product in the manner described in the procedure of Example III afforded 242 mg (93% yield) of material, shown by proton NMR analysis to contain a minor amount (approximately 25%) of unreacted starting ketone and allylic chlorides. Fractional evaporative distillation afforded 136 mg (52% yield, not corrected for recovery of starting materials) of the named unsaturated C-18 ketones: boiling point 115°-128° C. (bath temperature, 0.20 mm). The identity of this product mixture was confirmed by high-field (300 MHz) proton NMR analysis.

Provenance & Evidence