Tetrahydrofuran → 4-(Ethenyloxy)butyl prop-2-enoate

Participants

Reaction Steps

A 125 milliliter single-neck flask was charged with 11.6 grams (100 millimole) 4-hydroxybutylvinyl ether, 15.4 grams (150 millimoles) triethylamine, and twenty milliliters tetrahydrofuran. This solution was stirred magnetically and cooled in an ice bath. A solution of 9.05 grams (105 millimoles) acryloyl chloride dissolved in 20 milliliters THF was then dripped in over the course of forty-five minutes. The mix was stirred another hour while the temperature was allowed to rise to room temperature. The THF and excess triethylamine were removed on the rotary evaporator. The residue was extracted with three 20 ml portions of toluene and the toluene phase was rinsed with 20 ml deionized water. The toluene phase was dried with ten grams anhydrous magnesium sulfate and the toluene was removed to yield a mobile yellow liquid. The product weighed 12.3 grams (72% of theory). This liquid had major IR absorptions at 1723, 1635, 1616, 1408, 1188, 959, 809, and 731 wavenumbers.

Provenance & Evidence