Sodium hydride → Ethyl 2-[(4-iodophenyl)methyl]-3-oxoheptanoate

Participants

Reaction Steps

To a solution of 3.77 g (43.8 mmol) ethyl 3-oxoheptanoate in 200 mL DMSO was added 1.75 g (43.8 mmol) 65% NaH in oil. After 10 minutes, 6.5 g (21.9 mmol) α-bromo-4-iodotoluene was added. The mixture was allowed to stir for 2 hours. It was then poured into an ice/brine mixture and extracted 3 times with ether. The combined organic material was washed with brine, dried over MgSO4, stripped of solvent in vacuo, then Still flash chromatographed in 40% CH2Cl2 /hexane to give 2.46 g of the title compound, 29% yield. Rf 0.23 in 40% CH2Cl2 /hexane, visualized by UV and ninhydrin stain;

Provenance & Evidence