Allyl chloride → HCID 69380150, compound

Participants

Reaction Conditions

Reaction Steps

Mg metal turnings (0.33 g, 13.7 mmol) were placed in a clean, dry round bottom flask and flame-dried under vacuum. Freshly-distilled THF (2.5 mL) was added to the flask, and the contents were heated to reflux. The mixture was cooled to 40° C., and a solution of allyl chloride (0.75 mL, 0.70 g, 9.1 mmol) in THF (2.5 mL) was added dropwise over a 30 minute period. The resulting Grignard solution was held at 40° C. for an additional 20 minutes. The mixture was then cooled to −42° C. (dry ice/chlorobenzene bath), and a solution of the enone Compound 3 (0.5 g, 3 mmol) in THF (2.5 mL) was added dropwise. After 5 minutes, the cooling bath was removed, and the reaction was stirred for 1.5 hours as it warmed to room temperature. The mixture was then decanted into ice-cold 0.1 N HCl (50 mL) and extracted with ether. The combined organic fractions were washed with water and brine, dried over Na2SO4, filtered, and concentrated. Column chromatography (with 90:10/Hexane: EtOAc) provided Compound 4b (0.62 g, 98% yield) as a colorless liquid.

Provenance & Evidence