Acrolein → HCID 20245336, compound

Participants

Reaction Conditions

Reaction Steps

A dry, 3-necked flask equipped with argon inlet, stirring bar, and dropping funnel was charged sequentially with magnesium turnings (1.047 g, 43.05 g-atom) and a solution of 2-(2-bromoethyl)-1,3-dioxolane (6 g, 33.14 mmole) in tetrahydrofuran (70 ml). The reaction vessel was placed in an ultrasonic cleaning bath and subjected to sonication for 2.5 hours with occasional swirling while maintaining the bath temperature at 25°-30° C. The brown mixture was then cooled to -78° C. and treated dropwise with freshly distilled acrolein (2.21 ml, 33.14 mmole) in tetrahydrofuran (15 ml). The resulting thick mixture was stirred at -78° C. for an additional 30 minutes, the cooling bath was replaced with an ice bath and the reaction was quenched with a saturated sodium sulfate solution (ca. 30 ml), followed by solid sodium sulfate. The clear supernate was decanted from the precipitated solids which were washed with ethyl acetate (3×100 ml). The combined washings were dried (sodium sulfate), filtered, and concentrated in vacuo of 4.28 g of oil. The crude product was chromatographed on 140 g of silica gel (230-400 mesh) with 40% ethyl acetate:hexane to afford 2.41 g of the title compound as a clear, colorless oil.

Provenance & Evidence