Sodium Chloride → HCID 70237892, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3R,4S)-1-(2-tetrahydropyranyloxy)-3-((2E)-3-tributylstannyl-2-propene-1-yl)-4-methylazetidin-2-one (400 mg, 0.78 mmol) in 1 mL of dimethylformamide is added 4-bromotoluene (180 mg, 0.93 mmol) and triphenyphosphine palladium (II) dichloride (27 mg, 0.04 mmol). The resulting solution is heated at 80° C. for 18 h, then 1 mL ammonium hydroxide is added. The reaction mixture is poured into saturated sodium chloride solution (20 mL) and extracted wit 1:1 ethyl acetate/hexane (50 mL). The combined organic layers were dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography (elution with 3:1 hexanes-ethyl acetate) to provide (3R,4S)-1-(2-tetrahydropyranyloxy)-3-((2E)-3-(4-methylphenyl)-2-propene-1-yl)-4-methylazetidin-2-one as an oil (165 mg, 67% yield).

Provenance & Evidence