Butyl-l-heptyne

To a mixture of 0.10 mol of 1-ethoxy-l,2-heptadiene (see this chapter, Exp. 13) and 120 ml of diethyl ether was added 1 g of copper(I) bromide. A solution of butyl magnesium bromide in about 200 ml of diethyl ether, prepared from 0.25 mol of butyl bromide (see Chapter II, Exp. 5) was added in 15 min. The reaction was weakly exothermic and the temperature rose slowly to about 32°C. The mixture was held for an additional 40 min at that temperature, then the black reaction mixture was 

After the air in the flask had been replaced completely with nitrogen, 100 ml of dry diethyl ether, 0.20 mol of the cumulenic ether (see Chapter V, Exps. 7, 8 and 11) and 1 g (note 1) of copper(l) bromide were placed in it. A solution of the Grignard-reagent, prepared from 0.50 mol of the chloride (see Chapter II, 

Apparatus 1-1 flask, provided with a dropping funnel, combined with a gas inlet, a mechanical stirrer and an efficient reflux condenser. 

100 ml) was added dropwise with vigorous stirring until the refluxing of the diethyl 

---

In an analogous synthesis,23 3-butyl-l-heptyne was also characterized by mercuric oxide-sulfuric acid hydration4 to the known 3-butyl-2-heptanone,5 6 which also formed the known semicar-bazone.6... 

---