Sodium Chloride → HCID 70214140, 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 (0.92 g, 1.79 mmol) in 3 mL of dimethylformamide is added 4-chloroiodobenzene (470 mg, 1.97 mmol) and triphenyphosphine palladium (II) dichloride (63 mg, 0.09 mmol). The resulting solution is heated at 80° C. for 16 h, then 0.5 mL ammonium hydroxide is added. The reaction mixture is poured into saturated sodium chloride solution (20 mL) and extracted with 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-chlorophenyl)-2-propene-1-yl)-4-methylazetidin-2-one as an oil (370 mg, 61% yield).

Provenance & Evidence