Hydrochloric Acid → HCID 10955105, compound

Participants

Reaction Conditions

Reaction Steps

A diethyl ether solution (100 ml) of propargyl bromide (22.4 g, 190 mmols) was added dropwise to magnesium (5.20 g, 210 mmols) and HgCl2 (360 mg, 1.33 mmols) to obtain propargyl magnesium bromide (Grignard reagent). CuCl (200 mg, 2.02 mmols) was added to this Grignard reagent, and the resulting solution was ice-cooled. After a diethyl ether (100 ml) solution of (E)-1-bromo-3-methyl-2-dodecene (4′) (18.8 g, 72.0 mmols) was added dropwise, the mixture was stirred for 3 hours at 0° C. The reaction mixture was poured into ice water, acidified with diluted hydrochloric acid, and extracted several times with diethyl ether. The organic layers were combined, and washed with water and a saturated aqueous solution of sodium chloride. A small amount of allene type impurities was removed by silica gel column chromatography (elution with hexane) to obtain pure (E)-6-methyl-5-pentadecen-1-yne (5′) (12.7 g, 80%).

Provenance & Evidence