1- Ethoxy-l-propyne

Some studies seeking preferred conditions for this reaction have been reported. Optimum yields of 1-ethoxy-l-propyne and 1-ethoxy-l-butyne are found when the product is worked up before allowing the ammonia solvent to evaporate, as the product evidently volatilizes with the ammonia. An experiment with 1-ethoxy-l-propyne showed a marked increase in yield when ammonia predried over calcium hydride was used instead of ammonia directly from the cylinder. A twofold excess of ethyl bromide is required to obtain a good yield of 1-ethoxy-l-butyne, since elimination apparently competes with alkylation in this case. 

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