反应详情

To a stirring mixture of propiolic acid (1.79 mL (2.04 g), 28.65 mmol) and potassium carbonate (4.87 g, 35.2 mmol) in anhydrous DMF (40 mL) was added benzyl bromide (3.78 mL (5.43 g of 99% pure), 31.4 mmol). The reaction mixture was stirred at room temperature for 16 h. The resulting heterogeneous mixture was poured into 40 mL of H2O and was extracted with ethyl ether (3×40 mL). The combined ether extracts were dried (Na2SO4). Filtration and concentration provided 12.16 g of crude product, which upon high vacuum distillation yielded 2-propynoic acid phenylmethyl ester (bp 60° C. 0.5 mm) as a clear oil (3.57 g, 22.3 mmol) in 78% yield.

1. extractionwas extracted with ethyl ether (3×40 mL)
2. dry with materialThe combined ether extracts were dried (Na2SO4)
3. filtrationFiltration and concentration
4. customprovided 12.16 g of crude product, which
5. distillationupon high vacuum distillation