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; 1H-NMR (300 MHz, CDCl3): δ 7.58 (m,2H), 6.93 (m, 2H), 4.14 (m,2H), 3.72 (3 line m, 1H), 3.09 (m, 2H), 2.44 (12 line m, 2H), 1.50 (m, 2H), 1.22 (m, 2H), 1.21 (3 line m, 3H), 0.86 (3 line m, 3H).

Provenance & Evidence